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Synthesis of γ‐Boryl‐Substituted Homoallylic Alcohols with anti Stereochemistry Based on a Double‐Bond Transposition
Author(s) -
Miura Tomoya,
Nakahashi Junki,
Sasatsu Takanori,
Murakami Masahiro
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201811205
Subject(s) - chemistry , stereospecificity , double bond , stereoselectivity , transposition (logic) , stereochemistry , catalysis , organic chemistry , philosophy , linguistics
The stereoselective synthesis of anti isomers of γ‐boryl‐substituted homoallylic alcohols is disclosed. ( E )‐1,2‐Di(boryl)alk‐1‐enes undergo Ru‐catalyzed double‐bond transposition with control of the geometry. The in situ generated ( E )‐1,2‐di(boryl)alk‐2‐enes add to aldehydes in a stereospecific manner. The alkenylboron group within the product is amenable to a variety of synthetic derivatizations.