Asymmetric Pictet–Spengler Reactions Employing  N,N ‐Phthaloyl Amino Acids as Chiral Auxiliary Groups | Zendy

Waldmann Herbert | Zendy; Schmidt Gunther | Zendy; Henke Henning | Zendy; Burkard Michael | Zendy

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Asymmetric Pictet–Spengler Reactions Employing N,N ‐Phthaloyl Amino Acids as Chiral Auxiliary Groups

Author(s) -

Waldmann Herbert,

Schmidt Gunther,

Henke Henning,

Burkard Michael

Publication year - 1995

Publication title -

angewandte chemie international edition in english

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 0570-0833

DOI - 10.1002/anie.199524021

Subject(s) - diastereomer , chemistry , pictet–spengler reaction , amino acid , enantioselective synthesis , titanium , organic chemistry , stereochemistry , catalysis , biochemistry

Both aromatic and aliphatic Schiff bases 1 can be cyclized asymmetrically in the presence of titanium alkoxides if N,N ‐phthaloyl‐protected amino acids are employed as chiral auxiliaries. The desired heterocycles 3 , which are suitable for alkaloid syntheses, are formed with diastereomer ratios of up to 99%. R n Pr, i Pr; R 1 Me, Et, i Pr, Ph, Ar; R 2 Me, i Pr, t Bu.

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