Diastereoselective Addition of Prochiral Nucleophilic Alkenes to α-Chiral N-Sulfonyl Imines

被引：8

作者：

Gutierrez, David A. ^{[1
]}

Fettinger, James ^{[1
]}

Houk, K. N. ^{[2
]}

Ando, Kaori ^{[3
]}

Shaw, Jared T. ^{[1
]}

机构：

[1] Univ Calif Davis, Dept Chem, Davis, CA 95616 USA

[2] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

[3] Gifu Univ, Fac Engn, Dept Chem & Biomol Sci, Gifu 5011193, Japan

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 05期

基金：

美国国家科学基金会;

关键词：

STEREOCHEMICAL COURSE; ASYMMETRIC-SYNTHESIS; ANTI CROTYLATION; ALLYLATION; ALDEHYDES; TRIFLUOROBORATE; INDUCTION; MECHANISM; SYN;

D O I：

10.1021/acs.orglett.1c04219

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Lewis-acid-promoted addition of prochiral E- and Z-allyl nucleophiles to chiral alpha-alkoxy N-tosyl imines is described. Alkene geometry is selectively transferred to the newly formed carbon-carbon bond, resulting in stereochemical control of C1, C2, and C3 of the resulting 2-alkoxy-3-N-tosyl-4-alkyl-5-hexene products. A computational analysis to elucidate the high selectivity is also presented. This methodology was employed in the synthesis of two naturally occurring isomers of clausenamide.

引用

页码：1164 / 1168

页数：5

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