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Scientific article
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English

Complementary Catalytic Strategies to Access α-Chiral Aldehydes

ContributorsMazet, Clement
Published inChimia, vol. 67, no. 9, p. 658-662
Publication date2013
Abstract

The present article summarizes the development of two novel and complementary catalytic methods to access α-chiral aldehydes. A C 1-symmetric chiral (P,N) ligand with a structure derived from the ubiquitous binepine scaffold has been specifically designed for the Pd-catalyzed α-arylation of aldehydes to access indane derivatives with a well-defined quaternary stereocenter in high yields and excellent enantioselectivities. In addition, a dinuclear palladium hydride catalyst has been synthesized for the isomerization of terminal and trisubstituted epoxides into aldehydes and ketones respectively. Combined experimental and theoretical investigations pointed to an unprecedented 'epoxide-opening/hydride-transfer' sequence. The mechanism also features two distinct enantio-determining steps in the kinetic resolution of racemic epoxides.

Keywords
  • Aldehydes
  • Catalysis
  • Cross-Coupling
  • Isomerization
  • Palladium
Citation (ISO format)
MAZET, Clement. Complementary Catalytic Strategies to Access α-Chiral Aldehydes. In: Chimia, 2013, vol. 67, n° 9, p. 658–662. doi: 10.2533/chimia.2013.658
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Article (Published version)
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ISSN of the journal0009-4293
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Creation09/27/2013 4:09:00 PM
First validation09/27/2013 4:09:00 PM
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