Catalytic enantioselective reductive desymmetrisation of achiral and meso compounds

被引：38

作者：

Fernandez-Perez, Hector ^{[1
]}

Etayo, Pablo ^{[1
]}

Lao, Joan R. ^{[1
]}

Nunez-Ricoa, Jose L. ^{[1
]}

Vidal-Ferran, Anton ^{[1
,2
]}

机构：

[1] Inst Chem Res Catalonia ICIQ, E-43007 Tarragona, Spain

[2] Catalan Inst Res & Adv Studies ICREA, E-08010 Barcelona, Spain

来源：

CHEMICAL COMMUNICATIONS | 2013年 / 49卷 / 91期

关键词：

RING-OPENING REACTIONS; CHIRAL BUILDING-BLOCKS; ASYMMETRIC HYDROGENATION; CYCLIC ANHYDRIDES; ORGANIC-SYNTHESIS; 2,9-SUBSTITUTED 1,10-PHENANTHROLINES; ENZYMATIC DESYMMETRIZATIONS; BIFUNCTIONAL ADDITION; RUTHENIUM COMPLEXES; OXABICYCLIC ALKENES;

D O I：

10.1039/c3cc45466e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein an overview of reductive catalytic enantioselective desymmetrisation of achiral or meso compounds is provided. The most efficient reductive desymmetrisations described in the literature, which involve the reduction of C=O, C=N, C=C and C-halogen bonds, or reductive ring-opening, are summarised. The structural diversity of the valuable highly enantioenriched intermediates prepared by reductive desymmetrisation is highlighted.

引用

页码：10666 / 10675

页数：10

共 85 条

[51] Asymmetric Catalytic Hydrogenolysis of Aryl-Halide Bonds in Fused Arene Chromium and Ruthenium Complexes [J].

Mercier, Audrey ;

Urbaneja, Xavier ;

Yeo, Wee Chuan ;

Chaudhuri, Piyali Datta ;

Cumming, Graham R. ;

House, David ;

Bernardinelli, Gerald ;

Kuendig, E. Peter .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (21) :6285-6299

[52] Synthesis of highly enantiomerically enriched planar chiral ruthenium complexes via Pd-catalysed asymmetric hydrogenolysis [J].

Mercier, Audrey ;

Yeo, Wee Chuan ;

Chou, Jingyu ;

Chaudhuri, Piyali Datta ;

Bernardinelli, Gerald ;

Kuendig, E. Peter .

CHEMICAL COMMUNICATIONS, 2009, (35) :5227-5229

[53] Bronsted acid catalyzed asymmetric reduction of 2- and 2,9-substituted 1,10-phenanthrolines [J].

Metallinos, Costa ;

Barrett, Fred B. ;

Xu, Shufen .

SYNLETT, 2008, (05) :720-724

[54] Asymmetric desymmetrization: Simultaneous stereocontrol of multichiral centers [J].

Mikami, K ;

Yoshida, A .

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2002, 60 (08) :732-739

[55] Organocatalytic Enantioselective Acyl Transfer onto Racemic as well as meso Alcohols, Amines, and Thiols [J].

Mueller, Christian E. ;

Schreiner, Peter R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (27) :6012-6042

[56] Recent developments in asymmetric reduction of ketones with biocatalysts [J].

Nakamura, K ;

Yamanaka, R ;

Matsuda, T ;

Harada, T .

TETRAHEDRON-ASYMMETRY, 2003, 14 (18) :2659-2681

[57] Biocatalytic reduction of carbonyl groups [J].

Nakamura, Kaoru ;

Matsuda, Tomoko .

CURRENT ORGANIC CHEMISTRY, 2006, 10 (11) :1217-1246

[58] Stereoselectivity in the Rhodium-Catalysed Reductions of Non-Conjugated Dienes [J].

Nguyen, Bao ;

Brown, John M. .

ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (09) :1333-1343

[59] A short and practical access to both enantiomers of 4-hydroxycyclohexenone based on a desymmetrizing CBS reduction [J].

Nising, Carl F. ;

Ohnemueller, Ulrike K. ;

Braese, Stefan .

SYNTHESIS-STUTTGART, 2006, 16 (16) :2643-2645

[60]

Noyori R, 2001, ANGEW CHEM INT EDIT, V40, P40, DOI 10.1002/1521-3773(20010105)40:1<40::AID-ANIE40>3.0.CO

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