Enantioselective Synthesis of (E)-δ-Stannyl Homoallylic Alcohols via Aldehyde Allylboration Using α-Stannylallylboranes Generated by Allene Hydroboration Followed by a Highly Diastereoselective 1,3-Boratropic Shift

被引：51

作者：

Chen, Ming ^{[1
]}

Ess, Daniel H. ^{[1
]}

Roush, William R. ^{[1
]}

机构：

[1] Scripps Florida, Dept Chem, Jupiter, FL 33458 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 23期

基金：

美国国家卫生研究院;

关键词：

CATALYZED CARBONYL ALLYLATION; HALO BORONIC ESTERS; HIGH OPTICAL PURITY; ASYMMETRIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; OXIDATION LEVEL; GEOMETRIC ISOMERS; LEWIS-ACID; REAGENTS; ADDITIONS;

D O I：

10.1021/ja103041u

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly enantioselective synthesis of (E)-delta-stannyl homoallylic alcohols 4 via aldehyde allylboration reactions of the double-chiral allylborane reagent 2a is reported. Allylborane 2a was generated from the hydroboration of commercially available allenylstannane 1 with ((d)Ipc)(2)BH at -40 to -20 degrees C followed by a kinetically controlled and highly diastereoselective 1,3-boratropic shift in intermediate 3a.

引用

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页码：7881 / +

页数：4

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