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Development of asymmetric deacylative allylation.

ABSTRACT: Herein we present the development of asymmetric deacylative allylation of ketone enolates. The reaction directly couples readily available ketone pronucleophiles with allylic alcohols using facile retro-Claisen cleavage to form reactive intermediates in situ. The simplicity and robustness of the reaction conditions is demonstrated by the preparation of >6 g of an allylated tetralone from commercially available materials. Furthermore, use of nonracemic PHOX ligands allows intermolecular formation of quaternary stereocenters directly from allylic alcohols.

SUBMITTER: Grenning AJ

PROVIDER: S-EPMC3827786 | biostudies-literature | 2013 Jul

REPOSITORIES: biostudies-literature

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Development of asymmetric deacylative allylation.

Grenning Alexander J AJ Van Allen Christie K CK Maji Tapan T Lang Simon B SB Tunge Jon A JA

The Journal of organic chemistry 20130701 14

Herein we present the development of asymmetric deacylative allylation of ketone enolates. The reaction directly couples readily available ketone pronucleophiles with allylic alcohols using facile retro-Claisen cleavage to form reactive intermediates in situ. The simplicity and robustness of the reaction conditions is demonstrated by the preparation of >6 g of an allylated tetralone from commercially available materials. Furthermore, use of nonracemic PHOX ligands allows intermolecular formation ...[more]

PMID: 23734611

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