Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.



Reductive umpolung for asymmetric synthesis of chiral α-allenic alcohols

Author affiliations

Abstract

In this communication, we report a chiral copper/NHC-catalyzed reaction between aromatic aldehydes and propargylic phosphates using a silylboronate, providing enantioenriched chiral α-allenic alcohols with complete regioselectivity and moderate to high enantioselectivity. The reaction pathway involves the catalytic formation of a nucleophilic α-alkoxylalkylcopper(I) species from aldehydes followed by its SN2′ type substitution reaction with propargylic phosphates.

Graphical abstract: Reductive umpolung for asymmetric synthesis of chiral α-allenic alcohols

Back to tab navigation

Supplementary files

Article information


Submitted
11 Apr 2020
Accepted
27 May 2020
First published
27 May 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Reductive umpolung for asymmetric synthesis of chiral α-allenic alcohols

Y. Kondo, K. Nagao and H. Ohmiya, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC02619K

Social activity

Search articles by author

Spotlight

Advertisements