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Complex allylation by the direct cross-coupling of imines with unactivated allylic alcohols.

ABSTRACT: Regioselective, stereoselective: The convergent coupling of allylic alcohols with imines to deliver stereodefined homoallylic amines is described (see scheme). The process proceeds with net allylic transposition without the intermediacy of allylic organometallic reagents. Two stereodefined centers and a geometrically defined di- or trisubstituted alkene are forged with high selectivity.

SUBMITTER: Takahashi M

PROVIDER: S-EPMC3028933 | biostudies-literature | 2009

REPOSITORIES: biostudies-literature

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Complex allylation by the direct cross-coupling of imines with unactivated allylic alcohols.

Takahashi Masayuki M McLaughlin Martin M Micalizio Glenn C GC

Angewandte Chemie (International ed. in English) 20090101 20

Regioselective, stereoselective: The convergent coupling of allylic alcohols with imines to deliver stereodefined homoallylic amines is described (see scheme). The process proceeds with net allylic transposition without the intermediacy of allylic organometallic reagents. Two stereodefined centers and a geometrically defined di- or trisubstituted alkene are forged with high selectivity. ...[more]

PMID: 19360820

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Preparation of stereodefined homoallylic amines from the reductive cross-coupling of allylic alcohols with imines.

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