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The Synthesis of Enantiopure ω‐Methanoprolines and ω‐Methanopipecolic Acids by a Novel Cyclopropanation Reaction: The “Flattering” of Proline
Author(s) -
Hanessian Stephen,
Reinhold Ulrich,
Gentile Gabriella
Publication year - 1997
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.199718811
Subject(s) - cyclopropanation , enantiopure drug , peptidomimetic , proline , pipecolic acid , chemistry , ring (chemistry) , stereochemistry , combinatorial chemistry , amino acid , organic chemistry , enantioselective synthesis , catalysis , peptide , biochemistry
Conformationally constrained prolines ( 1,2 ) and pipecolic acids ( 3,4 ) can be synthesized stereoselectively by a novel cyclopropanation reaction. Considerable flattening of the ring can take place in the proline series. Such compounds for the preparation of peptidomimetics of therapeutic interest. Boc = tert ‐butoxycarbonyl.