Asymmetric Construction of Three Contiguous Stereogenic Centers by Conjugate Addition-Alkylation of Lithium Ester Enolate

被引：13

作者：

Yamamoto, Yasutomo ^{[1
]}

Yasuda, Yorinobu ^{[1
]}

Nasu, Hiroyuki ^{[1
]}

Tomioka, Kiyoshi ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 09期

关键词：

PINNAIC ACID; (+/-)-PINNAIC ACID; ORGANIC-SYNTHESIS; DOMINO REACTIONS; HALICHLORINE; CONCISE; CASCADE; TANDEM; (+/-)-HALICHLORINE; CONVENIENT;

D O I：

10.1021/ol900447n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A chiral ligand- and lithium amide-assisted asymmetric conjugate addition of lithium enolate of propionate to cyclopentenecarboxylate gave the corresponding lithium enolate, whose allylation gave the key intermediate of the marine alkaloid halichlorine as a single diastereomer with moderate enantioselectivity.

引用

页码：2007 / 2009

页数：3

共 2 条

[1] One-step stereocontrol of three contiguous stereogenic centers in acyclic systems: The tuning effect of an additive in a tandem asymmetric Michael addition and Meerwein-Ponndorf-Verley reduction
Nishide, K
Ozeki, M
Kunishige, H
Shigeta, Y
Patra, PK
Hagimoto, Y
Node, M
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (37) : 4515 - 4517
[2] The N-heterocyclic carbene-catalyzed [3+2] annulation of isoindigos with enals: the enantioselective construction of three contiguous stereogenic centers
Liu, Binghao
Qi, Jing
Wu, Yatong
Li, Jia-Hui
Li, Yanting
Duan, Xiao-Yong
ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (13) : 3552 - 3557

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