Recent Progress in Memory Of Chirality (MOC): An Advanced Chiral Pool

被引:53
作者
Alezra, Valerie [1 ]
Kawabata, Takeo [2 ]
机构
[1] Univ Paris Saclay, Univ Paris Sud, UMR 8182, ICMMO,Equipe Methodol Synth & Mol Therapeut,CNRS, Bat 410, F-91405 Orsay, France
[2] Kyoto Univ, Inst Chem Res, Uji, Kyoto 1110011, Japan
来源
SYNTHESIS-STUTTGART | 2016年 / 48卷 / 18期
关键词
memory of chirality; asymmetric synthesis; amino acids; chiral pool; dynamic chirality; AMINO-ACID DERIVATIVES; GOLD(I)-CATALYZED INTRAMOLECULAR CARBOALKOXYLATION; TERTIARY AROMATIC AMIDE; ENANTIOSELECTIVE SYNTHESIS; CONJUGATE ADDITION; AXIAL CHIRALITY; ASYMMETRIC CYCLIZATION; ALDOL REACTION; ELECTROCHEMICAL OXIDATION; CASCADE REARRANGEMENT;
D O I
10.1055/s-0035-1562441
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This review describes the recent advances in asymmetric reactions based on memory of chirality. The memory of chirality is a unique concept concerning an advanced type of chiral pool-based asymmetric synthesis, in which reactions take place at the sole stereogenic center of the starting materials. The original sp(3) chirality of the starting material is retained as dynamic sp(2) chirality in the intermediate, and then transferred to sp3 chirality of the product. These asymmetric reactions were found to proceed through various types of chiral intermediates with dynamic nature. This review describes the phenomena of memory of chirality observed in asymmetric reactions proceeding through radical, cationic, and anionic intermediates. 1 Introduction 2 Memory of Chirality Proceeding through Radical Intermediates 3 Memory of Chirality Proceeding through Cationic Intermediates 4 Memory of Chirality Proceeding through Anionic Intermediates 5 Conclusion
引用
收藏
页码:2997 / 3016
页数:20
相关论文
共 84 条
[1]  
[Anonymous], TOP STEREOCHEM
[2]   Enantioselective Deprotonative Ring Contraction of N1-Methyl-N4-Boc-benzo[e][1,4]cliazepine-2,5-diones [J].
Antolak, Stephanie A. ;
Yao, Zhong-Ke ;
Richoux, Gary M. ;
Slebodnick, Carla ;
Carlier, Paul R. .
ORGANIC LETTERS, 2014, 16 (19) :5204-5207
[3]   Ring Expansion of Cyclic β-Amino Alcohols Induced by Diethylaminosulfur Trifluoride: Synthesis of Cyclic Amines with a Tertiary Fluorine at C3 [J].
Anxionnat, Bruno ;
Robert, Benoit ;
George, Pascal ;
Ricci, Gino ;
Perrin, Marc-Antoine ;
Pardo, Domingo Gomez ;
Cossy, Janine .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (14) :6087-6099
[4]   A CYCLIZATION REACTION OF METHYL (4R)-3-(2-DIAZO-3-OXOBUTANOYL)THIAZOLIDINE-4-CARBOXYLATE WHICH PROCEEDS WITH RETENTION OF CONFIGURATION, PROBABLY VIA A PLANAR ESTER ENOLATE INTERMEDIATE POSSESSING AXIAL CHIRALITY [J].
BEAGLEY, B ;
BETTS, MJ ;
PRITCHARD, RG ;
SCHOFIELD, A ;
STOODLEY, RJ ;
VOHRA, S .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (14) :924-925
[5]   Tertiary aromatic amide for memory of chirality:: Access to enantioenriched α-substituted valine [J].
Branca, Mathieu ;
Gori, Didier ;
Guilot, Regis ;
Alezra, Valerie ;
Kouklovsky, Cyrille .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (18) :5864-+
[6]   Accurate conformation analysis in solution:: NMR and DFT/PCM study of the S-3-(1-naphthoyl)-4-isopropyl-2,2-dimethyloxazolidin-5-one in CDCl3 [J].
Branca, Mathieu ;
Alezra, Valerie ;
Kouklovsky, Cyrille ;
Archirel, Pierre .
TETRAHEDRON, 2008, 64 (08) :1743-1752
[7]   Memory of Chirality of Tertiary Aromatic Amides: A Simple and Efficient Method for the Enantioselective Synthesis of Quaternary α-Amino Acids [J].
Branca, Mathieu ;
Pena, Sebastien ;
Guillot, Regis ;
Gori, Didier ;
Alezra, Valerie ;
Kouklovsky, Cyrille .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (30) :10711-10718
[8]   Stereoselective intramolecular aldol reactions of (4R)-3-(3-oxobutanoyl)-1,3-thiazolidine-4-carboxylates believed to be directed by 'self-induced' axial chirality [J].
Brewster, AG ;
Frampton, CS ;
Jayatissa, J ;
Mitchell, MB ;
Stoodley, RJ ;
Vohra, S .
CHEMICAL COMMUNICATIONS, 1998, (03) :299-300
[9]   Memory of chirality effects in aldol cyclisations of 1-(3-oxobutyryl) derivatives of L-4-oxaproline and L-proline isopropyl esters [J].
Brewster, AG ;
Jayatissa, J ;
Mitchell, MB ;
Schofield, A ;
Stoodley, RJ .
TETRAHEDRON LETTERS, 2002, 43 (21) :3919-3922
[10]   Axial-to-central chirality transfer in cyclization processes [J].
Campolo, Damien ;
Gastaldi, Stephane ;
Roussel, Christian ;
Bertrand, Michele P. ;
Nechab, Malek .
CHEMICAL SOCIETY REVIEWS, 2013, 42 (21) :8434-8466