Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 43, Pages 17142-17145Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja207585p
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Funding
- American Chemical Society
- University of Delaware
- NIH [NSF MIR 0421224, NSF CRIF MU CHE0840401, CHE0541775, NIH P20 RR017716]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0840401] Funding Source: National Science Foundation
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We have developed an enantioselective, copper(I)-catalyzed addition of terminal alkynes to racemic isochroman acetals. This method is one of the first transition-metal-catalyzed approaches to enantioselective additions to prochiral oxocarbenium ions. In this reaction, TMSOTf is used to form the oxocarbenium ion in situ under conditions compatible with simultaneous formation of the chiral copper acetylide. By using a bis(oxazoline) ligand, good yields and enantioselectivities are observed for a variety of enantioenriched 1-alkynyl isochromans.
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