Highly chemo- and diastereoselective addition of diethylzinc through intramolecular autoactivation of enantiopure 2-acyl-1-formylferrocene:: application to the synthesis of optically pure 1,2-diacylferrocenes

被引：10

作者：

Malfait, S ^{[1
]}

Pélinski, L ^{[1
]}

Brocard, J ^{[1
]}

机构：

[1] Univ Sci & Technol Lille, Catalyse Heterogene & Homogene Lab, Grp Synth Organomet, CNRS,URA 402, F-59655 Villeneuve Dascq, France

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 13期

关键词：

D O I：

10.1016/S0957-4166(98)00238-9

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The enantiomerically pure 1,2-diacylferrocenes (+)-(R)-10-12 (ee>99%) were synthesized from (N,N-dimethylaminomethyl)ferrocene via enantiomerically pure 2-acyl-l-formylferrocene (+)-(R)-4-6. A novel methodology was performed using the chemo- and diastereoselective addition of diethylzinc to the formyl function through an intramolecular autoactivation. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

引用

页码：2207 / 2210

页数：4

共 4 条

[1] Umpolung Chemo- and Regioselective Cascade Addition of Diethylzinc to a-Diketones Followed by Intramolecular Michael Reaction: Stereoselective Synthesis of Highly Substituted 1-Indanones
Sar, Suman
Ghorai, Prasanta
[J]. ORGANIC LETTERS, 2022, 24 (36) : 6576 - 6581
[2] Diastereoselective 1,2-addition of organometallic reagents to chiral formylferrocenes leading to enantiomerically pure ferrocenyl amino alcohols: Application to asymmetric dialkylzinc addition to aldehydes and synthesis of optically active 1,2-homodisubstituted ferrocenes
Fukuzawa, S
Tsuchiya, D
Sasamoto, K
Hirano, K
Ohtaguchi, M
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2000, 2000 (16) : 2877 - 2883
[3] Highly diastereoselective addition of N-Boc-pyrrolidin-2-yllithium to optically active ketimines -: Synthesis of enantiomerically pure 1,3-imidazolidin-2-ones and diamines
von Keyserlingk, NG
Martens, J
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 2002 (02) : 301 - 308
[4] Highly efficient synthesis of chiral epoxides via borane reduction of 2-haloketones catalyzed by spiroborate ester: Application to the synthesis of optically pure 1,2-hydroxy ethers and 1,2-azido alcohols
Ortiz-Marciales, Margarita
Huang, Kun
Wang, Haiyang
De Jesus, Melvin
Torruellas, Carilyn
Correa, Wildeliz
Stepanenko, Viatcheslav
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240

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