Lewis Base Catalyzed Enantioselective Allylic Hydroxylation of Morita-Baylis-Hillman Carbonates with Water

被引：32

作者：

Zhu, Bo ^{[1
]}

Yan, Lin ^{[1
]}

Pan, Yuanhang ^{[2
]}

Lee, Richmond ^{[3
,4
]}

Liu, Hongjun ^{[2
]}

Han, Zhiqiang ^{[1
]}

Huang, Kuo-Wei ^{[3
,4
]}

Tan, Choon-Hong ^{[1
,2
]}

Jiang, Zhiyong ^{[1
]}

机构：

[1] Henan Univ, Key Lab Nat Med & Immunoengn Henan Prov, Kaifeng 475004, Henan, Peoples R China

[2] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore

[3] King Abdullah Univ Sci & Technol, KAUST Catalysis Ctr, Thuwal 239556900, Saudi Arabia

[4] King Abdullah Univ Sci & Technol, Div Chem & Life Sci & Engn, Thuwal 239556900, Saudi Arabia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 16期

基金：

中国国家自然科学基金;

关键词：

KINETIC RESOLUTION; GAMMA-BUTENOLIDES; PHOSPHINE OXIDES; ALKYLATION; SUBSTITUTION; REDUCTION; ALCOHOLS; ACETATES; KETONES; CONSTRUCTION;

D O I：

10.1021/jo201096e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Lewis base catalyzed allylic hydroxylation of Morita-Baylis-Hillman (MBH) carbonates has been developed. Various chiral MBH alcohols can be synthesized in high yields (up to 99%) and excellent enantioselectivities (up to 94% ee). This is the first report using water as a nucleophile in asymmetric organocatalysis. The nucleophilic role of water has been verified using O-18-labeling experiments.

引用

页码：6894 / 6900

页数：7

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