Transition-Metal-Free Formylation of Allylzinc Reagents Leading to α-Quaternary Aldehydes

被引：9

作者：

Haraguchi, Ryosuke ^{[1
]}

Kusakabe, Akinori ^{[1
]}

Mizutani, Nakaba ^{[1
]}

Fukuzawa, Shin-ichi ^{[1
]}

机构：

[1] Chuo Univ, Inst Sci & Engn, Dept Appl Chem, Bunkyo Ku, 1-13-27 Kasuga, Tokyo 1128551, Japan

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 06期

关键词：

CATALYZED ALLYLIC ALKYLATION; ASYMMETRIC MICHAEL ADDITION; BRANCHED ALDEHYDES; ALPHA; ALPHA-DISUBSTITUTED ALDEHYDES; ENANTIOSELECTIVE CONSTRUCTION; CARBON STEREOCENTERS; STEREOGENIC CENTERS; NATURAL-PRODUCTS; AMINO-ACID; ALLYLATION;

D O I：

10.1021/acs.orglett.8b00360

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first example of formylation of allylzinc reagents using S-phenyl thioformate is presented. The reaction proceeded under mild conditions without any transition-metal catalyst, forming quaternary carbon centers with reactive functionalities, such as formyl and vinyl groups. Moreover, Barbier-type formylation of an allylic bromide with a sterically demanding thioformate was achieved. As a preliminary result, asymmetric formylation was conducted using a menthol-derived chiral thioformate.

引用

页码：1613 / 1616

页数：4

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