Rhodium-catalyzed C-C Bond Cleavage: Construction of Acyclic Methyl Substituted Quaternary Stereogenic Centers

Overview

Journal J Am Chem Soc

Publisher American Chemical Society

Specialty Chemistry

Date 2010 Mar 30

PMID 20345153

Citations 20

Authors

Tobias Seiser

Nicolai Cramer

Affiliations

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Abstract

A rhodium-catalyzed enantioselective insertion into the C-C bond of tert-cyclobutanols and subsequent proto-demetalation provides access to methyl substituted quaternary stereogenic centers in excellent yields and enantioselectivities. The reaction was used for a synthesis of (S)-4-ethyl-4-methyl-octane, the simplest saturated hydrocarbon with a quaternary stereogenic center.

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