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FeCl₂-Mediated Rearrangement of Allylic Alcohols.

ABSTRACT: A mild, one-pot procedure to produce 3-substituted allylic alcohols from ?,?-unsaturated ketones is described. The addition of an organolithium nucleophile produces a tertiary allylic alcohol as an intermediate, which undergoes a 1,3-OH-migration assisted by FeCl₂. The proposed mechanism indicates that a syn-facial migration occurs for the major product. Yields as high as 98% for the one-pot reaction are reported.

SUBMITTER: Oppong-Quaicoe AA

PROVIDER: S-EPMC6648291 | biostudies-literature | 2019 Mar

REPOSITORIES: biostudies-literature

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FeCl2-Mediated Rearrangement of Allylic Alcohols.

Oppong-Quaicoe Anita A AA DeBoef Brenton B

ACS omega 20190329 3

A mild, one-pot procedure to produce 3-substituted allylic alcohols from α,β-unsaturated ketones is described. The addition of an organolithium nucleophile produces a tertiary allylic alcohol as an intermediate, which undergoes a 1,3-OH-migration assisted by FeCl2. The proposed mechanism indicates that a syn-facial migration occurs for the major product. Yields as high as 98% for the one-pot reaction are reported. ...[more]

PMID: 31459755

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