Synthesis 2015; 47(15): 2265-2269
DOI: 10.1055/s-0034-1378835
special topic
© Georg Thieme Verlag Stuttgart · New York

Conjugate Addition of Diboron Catalyzed by O-Monoacyltartaric Acids

Masaharu Sugiura*
Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Chuo-ku, Kumamoto 862-0973, Japan   Email: msugiura@kumamoto-u.ac.jp
,
Wakoto Ishikawa
Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Chuo-ku, Kumamoto 862-0973, Japan   Email: msugiura@kumamoto-u.ac.jp
,
Yukinobu Kuboyama
Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Chuo-ku, Kumamoto 862-0973, Japan   Email: msugiura@kumamoto-u.ac.jp
,
Makoto Nakajima
Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Chuo-ku, Kumamoto 862-0973, Japan   Email: msugiura@kumamoto-u.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 15 March 2015

Accepted after revision: 12 May 2015

Publication Date:
19 June 2015 (eFirst)

Abstract

O-3,5-Di(adamantan-1-yl)benzoyltartaric acid catalyzes the conjugate addition of bis(neopentyl glycolato)diboron to α,β-unsaturated ketones with good enantioselectivity. The addition of magnesium sulfate as a dehydrating agent and benzoic acid as a co-catalyst was found to be effective.

Supporting Information

 
  • References


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