Enantioselective Mukaiyama-Michael Reaction of β,γ-Unsaturated α-Keto Esters with Silyl Ketene Acetals Catalyzed by a Chiral Magnesium Phosphate

被引：5

作者：

He, Hualing ^{[1
]}

Shen, Xizhe ^{[1
]}

Ding, Xinying ^{[1
]}

Antilla, Jon C. ^{[1
]}

机构：

[1] Zhejiang Sci Tech Univ, Dept Chem, Hangzhou 310018, Zhejiang, Peoples R China

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 05期

关键词：

BINARY-ACID CATALYSIS; ASYMMETRIC-SYNTHESIS; CONJUGATE ADDITION; ENOL ETHERS; COMPLEXES; 1,4-ADDITION;

D O I：

10.1021/acs.orglett.2c04277

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We would like to describe an efficient and highly enantioselective Mukaiyama-Michael reaction of silyl ketene acetals with beta,gamma-unsaturated alpha-keto esters catalyzed by a chiral magnesium BINOL-derived phosphate. The resulting functionalized 1,5-dicarbonyl adducts are obtained in high yields (up to 96%) and with excellent enantioselectivities (up to 98%) under mild conditions. Two plausible mechanistic pathways were proposed, including a 1,4-addition and a hetero Diels-Alder [4 + 2] cycloaddition.

引用

页码：782 / 787

页数：6

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