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Synthesis 2015; 47(15): 2265-2269
DOI: 10.1055/s-0034-1378835
DOI: 10.1055/s-0034-1378835
special topic
Conjugate Addition of Diboron Catalyzed by O-Monoacyltartaric Acids
Weitere Informationen
Publikationsverlauf
Received: 15. März 2015
Accepted after revision: 12. Mai 2015
Publikationsdatum:
19. Juni 2015 (online)
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
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1378835.
- Supporting Information
-
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In addition to the conjugate addition, there are several enantioselective reactions for the construction of chiral carbon centers attached to boryl groups: borane or diboron additions to alkenes, allylic substitution, and diboron addition to imines. For a review on hydroboration, see:
For a leading reference on diboration of alkenes, see:
For a leading reference on proto-boration, see:
For a leading reference on allylic substitution, see:
For leading references on diboron addition to imines, see:
For leading references on enantioselective copper catalysis, see:
For enantioselective rhodium catalysis, see:
For enantioselective nickel and palladium catalysis, see:
For related catalytic mechanisms, see: