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Asymmetric synthesis of ?-alkenyl homoallylic primary amines via 1,2-addition of Grignard reagent to ?,?-unsaturated phosphonyl imines.

ABSTRACT: A series of chiral N-phosphonyl protected ?-alkenyl homoallylic primary amines were synthesized by asymmetric addition of allylmagnesium bromide Grignard reagent towards chiral ?,?-unsaturated imines. Only 1,2-adduct was obtained for all the imines with good yields and excellent diastereoselectivities. The chiral auxiliary could be easily removed under simple conditions, giving free multiple functionalized primary amines.

SUBMITTER: Xiong Y

PROVIDER: S-EPMC3804338 | biostudies-literature | 2013 Jan

REPOSITORIES: biostudies-literature

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Asymmetric synthesis of α-alkenyl homoallylic primary amines via 1,2-addition of Grignard reagent to α,β-unsaturated phosphonyl imines.

Xiong Yiwen Y Mei Haibo H Xie Chen C Han Jianlin J Li Guigen G Pan Yi Y

RSC advances 20130101 36

A series of chiral <i>N</i>-phosphonyl protected α-alkenyl homoallylic primary amines were synthesized by asymmetric addition of allylmagnesium bromide Grignard reagent towards chiral α,β-unsaturated imines. Only 1,2-adduct was obtained for all the imines with good yields and excellent diastereoselectivities. The chiral auxiliary could be easily removed under simple conditions, giving free multiple functionalized primary amines. ...[more]

PMID: 24159373

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