Title

Pentanidium-Catalyzed Direct Assembly of Vicinal All-Carbon Quaternary Stereocenters through C(sp3)–C(sp3) Bond Formation

Publication Name

CCS Chemistry

Abstract

The stereoselective construction of vicinal all-carbon quaternary stereocenters has long been a formidable synthetic challenge. Direct asymmetric coupling of a tertiary carbon nucleophile with a tertiary carbon electrophile is the most straightforward approach, but it is sterically and energetically disfavored. Herein, we describe a catalytic asymmetric substitution, where racemic tertiary bromides coupled directly with racemic secondary or tertiary carbanion, creating a series of congested C(sp3)–C(sp3) bonds, including isolated all-carbon quaternary stereocenters, vicinal tertiary/all-carbon quaternary stereocenters and vicinal all-carbon quaternary stereocenters. Using pentanidium as a catalyst, this double stereoconvergent process afforded substituted products in good enantioselectivities and diastereoselectivities.

Open Access Status

This publication may be available as open access

Volume

3

Issue

10

First Page

2192

Last Page

2200

Funding Number

DECRA DE210100053

Funding Sponsor

Australian Research Council

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Link to publisher version (DOI)

http://dx.doi.org/10.31635/ccschem.021.202101013