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Stereodivergent Intramolecular C(sp3)–H Functionalization of Azavinyl Carbenes: Synthesis of Saturated Heterocycles and Fused N-Heterotricycles

Authors
Type
Published Article
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society
Publication Date
Jan 14, 2015
Volume
137
Issue
26
Pages
137–8368
Identifiers
DOI: 10.1021/jacs.5b04295
Source
CCHF
License
White

Abstract

A general approach for the formation of five-membered saturated heterocycles by intramolecular C(sp3)–H functionalization is reported. Using N-sulfonyltriazoles as Rh(II) azavinyl carbene equivalents, a wide variety of stereodefined cis-2,3-disubstituted tetrahydrofurans were obtained with good to excellent diastereoselectivity from readily available acyclic precursors. The reaction is shown to be amenable to gram scale, and judicious choice of reaction conditions allowed for stereodivergence, providing selective access to the trans diastereomer in good yield. The resulting products were shown to be valuable intermediates for the direct preparation of fused N-heterotricycles in one step by intramolecular C–H amination or Pictet–Spengler cyclization.

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