Asymmetric synthesis of β‐amino acids and α‐deuterated β‐amino acids via conjugate addition of homochiral amidocuprates | Zendy

Sewald Norbert | Zendy; Hiller Klaus D. | Zendy; Helmreich Brigitte | Zendy

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Asymmetric synthesis of β‐amino acids and α‐deuterated β‐amino acids via conjugate addition of homochiral amidocuprates

Author(s) -

Sewald Norbert,

Hiller Klaus D.,

Helmreich Brigitte

Publication year - 1995

Publication title -

liebigs annalen

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 0947-3440

DOI - 10.1002/jlac.1995199505133

Subject(s) - chemistry , conjugate , amino acid , stereoselectivity , amine gas treating , deuterium , stereochemistry , enantioselective synthesis , combinatorial chemistry , organic chemistry , catalysis , biochemistry , mathematical analysis , physics , mathematics , quantum mechanics

Conjugate addition of homochiral amidocuprates based on N ‐[( R )‐1‐phenylethyl]trimethylsilylamine or bis[( R )‐1‐phenylethyl]amine to α,β‐unsaturated esters provides an efficient methodology for the asymmetric synthesis of β‐amino acids. Trapping of the intermediate enolate with D 2 O yields α‐deuterated β‐amino acids with excellent stereoselectivity.

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