Synthesis of γ‐Boryl‐Substituted Homoallylic Alcohols with  anti  Stereochemistry Based on a Double‐Bond Transposition | Zendy

Miura Tomoya | Zendy; Nakahashi Junki | Zendy; Sasatsu Takanori | Zendy; Murakami Masahiro | Zendy

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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.

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