Trialkylborane-Mediated Multicomponent Reaction for the Diastereoselective Synthesis of Anti-δ,δ-Disubstituted Homoallylic Alcohols

被引：3

作者：

Horino, Yoshikazu ^{[1
]}

Murakami, Miki ^{[1
]}

Aimono, Ataru ^{[1
]}

Lee, Jun Hee ^{[2
]}

Abe, Hitoshi ^{[1
]}

机构：

[1] Univ Toyama, Grad Sch Sci & Engn, 3190 Gofuku, Toyama 9308555, Japan

[2] Dongguk Univ, Dept Adv Mat Chem, Gyeongju 780714, South Korea

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 02期

关键词：

3-COMPONENT COUPLING REACTIONS; STEREOSELECTIVE-SYNTHESIS; ARYLBORONIC ACIDS; ORGANIC-SYNTHESIS; FACILE REACTION; STILLE REACTION; ALKYNES; CARBOSTANNYLATION; ALKYNYLSTANNANES; ALDEHYDES;

D O I：

10.1021/acs.orglett.8b03761

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The trialkylborane/O-2-mediated reaction of propargyl acetates having a tributylstannyl group at an alkyne terminus with aldehydes in a THF-H2O solvent system gave anti-delta,delta-disubstituted homoallylic alcohols with good to high diastereoselectivity. Intriguingly, two alkyl groups derived from trialkylborane were embedded into the reaction product. The trialkylborane plays a key role not only as a radical initiator but also as a source of alkyl radicals.

引用

页码：476 / 480

页数：5

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