Enantioselective, Lewis Base-Catalyzed Carbosulfenylation of Alkenylboronates by 1,2-Boronate Migration

Zhonglin Tao, Kevin A. Robb, Jesse L. Panger, Scott E Denmark

Research output: Contribution to journalArticle

Abstract

A catalytic, enantioselective method for the preparation of chiral, non-racemic, alkylboronic esters bearing two vicinal stereogenic centers is described. The reaction proceeds via a 1,2-migration of a zwitterionic thiiranium-boronate complex to give exclusively anti carbosulfenylation products. A broad scope of aryl groups migrate with good yield and excellent enantioselectivity (up to 99:1 e.r.). Similarly, a range of di- and trisubstituted alkenylboronic esters are competent reaction partners. This method provides access to both secondary and tertiary chiral alkylboronic esters.

Original languageEnglish (US)
Pages (from-to)15621-15625
Number of pages5
JournalJournal of the American Chemical Society
Volume140
Issue number46
DOIs
StatePublished - Nov 21 2018

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Lewis Bases
ester
Esters
Bearings (structural)
Enantioselectivity
method

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Enantioselective, Lewis Base-Catalyzed Carbosulfenylation of Alkenylboronates by 1,2-Boronate Migration. / Tao, Zhonglin; Robb, Kevin A.; Panger, Jesse L.; Denmark, Scott E.

In: Journal of the American Chemical Society, Vol. 140, No. 46, 21.11.2018, p. 15621-15625.

Research output: Contribution to journalArticle

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