The Synthesis of Enantiopure ω‐Methanoprolines and ω‐Methanopipecolic Acids by a Novel Cyclopropanation Reaction: The “Flattering” of Proline | Zendy

Hanessian Stephen | Zendy; Reinhold Ulrich | Zendy; Gentile Gabriella | Zendy

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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.

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