Work

Highly (E)-Selective BF3·Et2O-Promoted Allylboration of Chiral Nonracemic α-Substituted Allylboronates and Analysis of the Origin of Stereocontrol

Year: 2010

Type: article

Abstract: Delta-methyl-substituted homoallylic alcohols 2 were prepared in 71-88% yield, E:Z >30:1 and 93% to >95% ee via BF(3).Et(2)O-promoted allylboration with alpha-Me-allylboronate 1. The origin of high (E)-selectivity is proposed.

Source: Organic Letters

DOI: 10.1021/ol1007444

Authors: Ming Chen, William R. Roush

Institution: Scripps Institution of Oceanography

Language: English

Topic: Organoboron and organosilicon chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Awards: G1361127007, G425255249, G5954913868, Natural Products Synthesis via Cycloaddition Reactions, G918211471

OpenAlex ID: W1964555670

FWCI: 3.012

Cites: 104

Cited by: 62

Related to: 10