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Lewis Acid Catalyzed Borotropic Shifts in the Design of Diastereo- and Enantioselective ?-Additions of Allylboron Moieties to Aldimines.

ABSTRACT: Catalytic allylboron additions to aldimines are presented for which small amounts of Zn(OMe)2 serve as the co-catalyst to accelerate allyl exchange and 1,3-borotropic shift processes. Low-yielding and moderately ?- and diastereoselective reactions are thus turned into highly efficient ?-, diastereo-, and enantioselective transformations that exhibit considerable scope.

SUBMITTER: van der Mei FW

PROVIDER: S-EPMC4973465 | biostudies-literature | 2016 Apr

REPOSITORIES: biostudies-literature

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Lewis Acid Catalyzed Borotropic Shifts in the Design of Diastereo- and Enantioselective γ-Additions of Allylboron Moieties to Aldimines.

van der Mei Farid W FW Miyamoto Hiroshi H Silverio Daniel L DL Hoveyda Amir H AH

Angewandte Chemie (International ed. in English) 20160309 15

Catalytic allylboron additions to aldimines are presented for which small amounts of Zn(OMe)2 serve as the co-catalyst to accelerate allyl exchange and 1,3-borotropic shift processes. Low-yielding and moderately α- and diastereoselective reactions are thus turned into highly efficient γ-, diastereo-, and enantioselective transformations that exhibit considerable scope. ...[more]

PMID: 26961497

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