铑催化剂催化烯烃不对称加氢反应研究进展

doi:10.16085/j.issn.1000-6613.2016.02.021

摘要/Abstract

摘要： 不对称催化氢化反应具有完美的原子经济性和清洁高效等特点,是最受青睐的不对称合成方法之一。C=C、C=O、C=N的不对称加氢反应仍主要依赖过渡金属催化剂。过渡金属催化剂,尤其是铑催化剂,催化碳碳双键的不对称加氢反应仍是一个不断发展的领域。本文对近年来利用铑催化剂催化烯烃进行不对称氢化反应的研究进展进行了综述,着重介绍了铑-双膦配体催化体系催化烯烃不对称加氢反应的催化机理,以及铑催化剂在烯胺、不饱和羧酸及衍生物、烯醇酯和非官能团烯烃不对称氢化中的应用,并通过对现有文献的总结指出了今后铑催化剂催化烯烃氢化反应的研究重点,即:①铑-单膦配体催化烯烃不对称氢化反应的作用机理须待提出;②非官能化底物不对称催化氢化反应的手性配体亟待拓宽。

关键词: 催化剂, 选择性, 加氢, 烯烃, 催化机理, 配合物

Abstract: Asymmetric hydrogenation has the advantage of cleanliness,perfect atom economy,and is one of the hottest methods of asymmetric synthesis. The asymmetric hydrogenation in C=C,C=O,C=N are still primarily dependent on the use of transition metal catalysts. The study of transition metal catalysts,especially the asymmetric hydrogenation of carbon-carbon double bond catalyzed by rhodium catalysts is still an evolving field. In the present review,the progress on asymmetric hydrogenation of olefins catalyzed by rhodium catalysts are described,including the catalytic mechanism of rhodium-diphosphine ligand catalyst system,the application of asymmetric hydrogenation of enamines,unsaturated carboxylic acids and their derivatives,enol ester as well as unfunctionalized olefins catalyzed by rhodium catalysts. The development trend of rhodium catalysts for asymmetric hydrogenation of olefins was pointed out. For instance:① the catalytic mechanism of asymmetric hydrogenation of olefins by rhodium-monophosphine ligand needs to be understood; ② more chiral ligands for asymmetric hydrogenation of unfunctionalized olefins are still wanted.

Key words: catalyst, selectivity, hydrogenation, olefin, catalytic mechanisms, complexes

中图分类号:

O643

王红琴, 蒋丽红, 王亚明. 铑催化剂催化烯烃不对称加氢反应研究进展[J]. 化工进展, 2016, 35(02): 485-492.

WANG Hongqin, JIANG Lihong, WANG Yaming. Research progress of olefins asymmetric hydrogenation catalyzed by rhodium catalysts[J]. Chemical Industry and Engineering Progree, 2016, 35(02): 485-492.

参考文献

[1] KNOWLES W S,SABACKY M J. Catalytic asymmetric hydrogenation employing a soluble,optically active,rhodium complex[J]. Chemical Communications,1968,22:1445-1446.
[2] KNOWLES W S. Application of organometallic catalysis to the commercial production of L-DOPA[J]. Journal of Chemical Education,1986,63(3):222-225.
[3] 陈传杰,魏作君. 铱-氮膦配体催化剂在非官能化烯烃不对称氢化中的研究[J]. 化学进展,2009,21(5):990-996.
[4] INAGAKI Fuyuhiko,MUKAI Chisato. Rhodium(I)-catalyzed intramolecular pauson-khand-type [2+2+1] cycloaddition of allenenes[J]. Org. Lett.,2006,8(6):1217-1220.
[5] 吴跃,薛屏. 多相手性催化剂的制备及其对不对称加氢反应的催化作用[J]. 化工进展,2006,25(11):1301-1308.
[6] 何年志,张学勤,肖美添. 手性修饰催化剂在多相不对称氢化中的研究进展[J]. 化工进展,2012,31(12):2694-2701,2719.
[7] HALPERN J. Mechanism and stereoseIectivity of asymmetric hydrogenation[J]. Science,1982,217(4558):401-407.
[8] CHAN A S C,HALPERN J. Interception and characterization of a hydridoalkylrhodium intermediate in a homogeneous catalytic hydrogenation reaction[J]. Journal of the American Chemical Society,1980,102(2):838-840.
[9] LANDIS C R,HALPERN J. Asymmetric hydrogenation of methyl (Z)-alpha-acetamidocinnamate catalyzed by [1,2-bis(phenyl-o-anisoyl) phosphino) ethane] rhodium (I):kinetics,mechanism and origin of enantioselection[J]. Journal of the American Chemical Society,1987,109(6):1746-1754.
[10] CHAN A S C,PLUTH J J,HALPERN J. Identification of the enantioselective step in the asymmetric catalytic hydrogenation of a prochiral olefin[J]. Journal of the American Chemical Society,1980,102(18):5952-5954.
[11] LANDIS C R,FELDGUS S. A simple model for the origin of enantioselection and the anti “Lock-and Key” motif in asymmetric hydorgenation of enamides as catalyzed by chiral diphosphine complexes of Rh(I)[J]. Angew. Chem. Int. Ed.,2000,39(16):2863-2866.
[12] BURK Mark J,WANG Yanming,LEE Jeffrey R. A convenient asymmetric synthesis of α-1-arylalkylamines through the enantioselective hydrogenation of enamides[J]. J. Am. Chem. Soc.,1996,118(21):5142-5143.
[13] BURK MARK J,CASY Guy,JOHNSON Nicholas B. A three-step procedure for asymmetric catalytic reductive amidation of ketones[J]. J. Org. Chem.,1998,63(18):6084-6085.
[14] JIA Xian,GUO Rongwei,LI Xingshu,et al. Highly enantioselective hydrogenation of enamides catalyzed by rhodium-monodentate phosphoramidite complex[J]. Tetrahedron Letters,2002,43(32):5541-5544.
[15] VAN DEN BERG M,HAAK RobertM,MINNAARD AdriaanJ,et al. Rhodium/monophos-catalyzed asymmetric hydrogenation of enamides[J]. Adv. Synth. Catal.,2002,344(9):1003-1007.
[16] VAN DEN BERG Michel,HAAK RobertM,MINNAARD AdriaanJ,et al. Monodentate phosphoramidites:a breakthrough in rhodium-catalysed asymmetric hydrogenation of olefins[J]. Adv. Synth. Catal.,2003,345(1):308-323.
[17] JIA Xian,LI Xingshu,XU Lijin,et al. Highly efficient rhodium/monodentate phosphoramidite catalyst and its application in the enantioselective hydrogenation of enamides and α-dehydroamino acid derivatives[J]. J. Org. Chem.,2003,68(11):4539-4541.
[18] BERNSMANN Heiko,VAN DEN BERG Michel,HOEN Rob,et al. Pipphos and morfphos:privileged monodentate phosphoramidite ligands for rhodium-catalyzed asymmetric hydrogenation[J]. J. Org. Chem.,2005,70(3):943-951.
[19] LI Xingshu,JIA Xian,LU Gui,et al. Highly enantioselective hydrogenation of enamides catalyzed by rhodium-monodentate phosphoramidite complex derived from H₈-BINOL[J]. Tetrahedron:Asymmetry,2003,14(18):2687-2691.
[20] 段正超,王联芝,胡向平,等. 衍生于手性双二茂铁乙胺的单齿亚磷酰胺配体在不对称催化氢化中的应用[J]. 分子催化,2012,26(4):328-332.
[21] LI Wenjie,RODRIGUEZ Sonia,DURAN Adil,et al. The P-chiral phosphane ligand (MeO-BIBOP) for efficient and practical large-scale Rh-catalyzed asymmetric hydrogenation of N-acetyl enamides with high TONs[J]. Org. Process Res. Dev.,2013,17(8):1061-1065.
[22] JIANG Jun,WANG Yan,ZHANG Xumu. Rhodium-catalyzed asymmetric hydrogenation of β-acetylamino acrylosulfones:a practical approach to chiral β-amido sulfones[J].ACS Catal.,2014,4(5):1570- 1573.
[23] BLASER Hans-Ulrich,PUGIN Benoît,SPINDLER Felix. Progress in enantioselective catalysis assessed from an industrial point of view[J]. Journal of Molecular Catalysis A:Chemical,2005,231(1-2):1-20.
[24] VITTORIO Farina,REEVES Jonathan T,SENANAYAKE Chris H,et al. Asymmetric synthesis of active pharmaceutical ingredients[J]. Chem. Rev.,2006,106(7):2734-2793.
[25] FRAMPTON James E,CURRAN Monique P. Aliskiren:a review of its use in the management of hypertension[J]. Drugs,2007,67(12):1767-1792.
[26] LEFORT Laurent,BOOGERS Jeroen A F,DEVRIES André H M,et al. High throughput screening of monophos instant ligand library leads to a ton-scale asymmetric hydrogenation process[J]. Topics in Catalysis,2006,40(1/2/3/4):185-191.
[27] BOOGERS Jeroen A F,FELFER Ulfried,KOTTHAUS Martina,et al. A mixed-ligand approach enables the asymmetric hydrogenation of an α-isopropylcinnamic acid en route to the renin inhibitor aliskiren[J]. Org. Process Res. Dev.,2007,11(3):585-591.
[28] STURM Thomas,WEISSENSTEINER Walter,SPINDLER Felix,et al. A novel class of ferrocenyl-aryl-based diphosphine ligands for Rh- and Ru-catalysed enantioselective hydrogenation[J]. Adv. Synth. Catal.,2003,345(1/2):160-164.
[29] CHEN Weiping,MCCORMACK Peter J,MOHAMMED Karim,et al. Stereoselective synthesis of ferrocene-based C₂-symmetric diphosphine ligands:application to the highly enantioselective hydrogenation of alpha-substituted cinnamic acids[J]. Angew. Chem.,2007,119(22):4219-4222.
[30] ANDRUSHKO Natalia,ANDRUSHKO Vasyl,THYRANN Thomas,et al. Synthesis of enantiopure (R)-2-[4-methoxy-3- (3-methoxypropoxy)-benzyl]-3-methylbutanoic acid—a key intermediate for the preparation of Aliskiren[J]. Tetrahedron Letters,2008,49(41):5980-5982.
[31] YANG Meng,ZHANG Ji,WANG Na,et al. A new class of polymeric monodentate phosphoramidite ligands for asymmetric hydrogenation of α-dehydroamino acid derivatives[J]. ARKIVOC,2008,28(16):279-287.
[32] FARKAS Gergely,BALOGH Szabolcs,SZÖLLŐSYET Áron,et al. Novel phosphine-phosphites and their use in asymmetric hydrogenation[J]. Tetrahedron:Asymmetry,2011,22(24):2104-2109.
[33] 刘龑,王正,丁奎岭. DpenPhos/Rh(I)催化的β-脱氢氨基酸酯的不对称氢化反应[J]. 化学学报,2012,70(13):1464-1470.
[34] IMAMOTO Tsuneo,TAMURA Ken,ZHANG Zhenfeng,et al. Rigid P-chiral phosphine ligands with tert-butylmethylphosphino groups for rhodium-catalyzed asymmetric hydrogenation of functionalized alkenes[J]. J. Am. Chem. Soc.,2012,134(3):1754-1769.
[35] GHEORGHIU C C,DE LECEA C S M,MACHADO B F,et al. Chiral rhodium complexes covalently anchored on carbon nanotubes for enantioselective hydrogenation[J]. Dalton Trans.,2014,43(20):7455-7463.
[36] 苗晓,李海峰,逄增波,等. D-甘露醇衍生的手性亚磷酸酯配体:合成及应用于铑催化α-脱氢氨基酸酯不对称氢化[J]. 分子催化,2014,28(5):393-399.
[37] HUANG H M,ZHENG Z,LUO H L,et al. A novel class of P-O monophosphite ligands derived from D-mannitol:broad applications in highly enantioselective Rh-catalyzed hydrogenations[J]. The Journal of organic chemistry,2004,69(7):2355-2361.
[38] LIU Y,WANG Z,DING K. Rh (I)/DpenPhos catalyzed asymmetric hydrogenation of enol esters and potassium (E)-3-cyano-5-methylhex-3- enoate[J]. Tetrahedron,2012,68(37):7581-7585.
[39] KLEMAN P,GONZÁLEZ-LISTE P J,GARCÍA-GARRIDO S E,et al. Highly enantioselective hydrogenation of 1-alkylvinyl benzoates:a simple,nonenzymatic access to chiral 2-alkanols[J]. Chemistry—A European Journal,2013,19(48):16209-16212.
[40] PANELLA L,FERINGA B L,DE VRIES J G,et al. Enantioselective Rh-catalyzed hydrogenation of enol acetates and enol carbamates with monodentate phosphoramidites[J]. Organic Letters,2005,7(19):4177-4180.
[41] WANG D Y,HU X P,HUANG J D,et al. Highly enantioselective synthesis of α-hydroxy phosphonic acid derivatives by Rh-catalyzed asymmetric hydrogenation with phosphine-phosphoramidite ligands[J]. Angewandte Chemie,2007,119(41):7956-7959.
[42] YU S B,HUANG J D,WANG D Y,et al. Novel chiral phosphine-phosphoramidite ligands derived from 1-naphthylamine for highly efficient Rh-catalyzed asymmetric hydrogenation[J]. Tetrahedron:Asymmetry,2008,19(15):1862-1866.
[43] 胡娟,王道永,郑卓,等. 苯乙胺衍生的手性膦-亚磷酰胺酯配体在 Rh-催化α-烯醇酯膦酸酯的不对称氢化反应中的应用[J]. 分子催化,2012,26(6):487-492.
[44] SUAREZ P A Z,DULLIUS J E L,EINLOFT S,et al. The use of new ionic liquids in two-phase catalytic hydrogenation reaction by rhodium complexes[J]. Polyhedron,1996,15(7):1217-1219.
[45] LIU F,ABRAMS M B,BAKER R T,et al. Phase-separable catalysis using room temperature ionic liquids and super critical carbon dioxide[J]. Chemical Communications,2001,1(5):433-434.
[46] PEREZ-CADENAS M,LEMUS-YEGRES L J,ROMÁN- MARTÍNEZ M C,et al. Immobilization of a Rh complex derived from the Wilkinson’s catalyst on activated carbon and carbon nanotubes[J]. Applied Catalysis A:General,2011,402(1-2):132-138.
[47] SILBERNAGEL Rita,DÍAZ Agustín,STEFFENSMEIERET Eric,et al. Wilkinson-type hydrogenation catalysts immobilized on zirconium phosphate nanoplatelets[J]. Journal of Molecular Catalysis A:Chemical,2014,394:217-223.
[48] 蒋丽红. 一种由α-蒎烯不对称催化加氢制备顺式蒎烷的方法:201410183712.1[P]. 2014-05-05.