Magnesium–Tartramide Complex Mediated Asymmetric Strecker-Type Reaction of Nitrones Using Cyanohydrin | Zendy

Takahiro Sakai | Zendy; Takahiro Soeta | Zendy; Kohei Endo | Zendy; Shuhei Fujinami | Zendy; Yutaka Ukaji | Zendy

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Magnesium–Tartramide Complex Mediated Asymmetric Strecker-Type Reaction of Nitrones Using Cyanohydrin

Author(s) -

Takahiro Sakai,

Takahiro Soeta,

Kohei Endo,

Shuhei Fujinami,

Yutaka Ukaji

Publication year - 2013

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol400898p

Subject(s) - cyanohydrin , chemistry , strecker amino acid synthesis , catalysis , nitrile , acetone , organic chemistry , butane , salt (chemistry) , enantioselective synthesis

An asymmetric Strecker-type reaction of nitrones using acetone cyanohydrin as a source of HCN has been realized. A magnesium-tartramide complex, generated from (R,R)-2,3-dihydroxy-1,4-di(pyrrolidin-1-yl)-butane-1,4-dione and MeMgBr, promoted transcyanation from the bromomagnesium salt of the cyanohydrin, in the presence of a catalytic amount of DBU, to afford the corresponding optically active (S)-α-amino nitrile derivatives. The reaction was applicable to various nitrones giving high-to-excellent enantioselectivities.

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