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Article

Synthesis of P,N-Heterocycles from ω-Amino-H-Phosphinates: Conformationally Restricted α-Amino Acid Analogs

Supporting Info

mence Queffelec, Patrice Ribi

re and Jean-Luc Montchamp*

Department of Chemistry, Box 298860, Texas Christian University, Fort Worth, Texas 76129

J. Org. Chem., 2008, 73 (22), pp 8987–8991

DOI: 10.1021/jo801768y

Publication Date (Web): October 15, 2008

Abstract

P,N-Heterocycles (3-hydroxy-1,3-azaphospholane and 3-hydroxy-1,3-azaphosphorinane-3-oxide) are synthesized in moderate yield from readily available ω-amino-H-phosphinates and aldehydes or ketones via an intramolecular Kabachnik−Fields reaction. The products are conformationally restricted phosphinic analogs of α-amino acids. The multigram-scale syntheses of the H₂N(CH₂)_nPO₂H₂ phosphinic precursors (n = 1, 2, 3) and some derivatives are also described.

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Published In Issue November 21, 2008
Article ASAPOctober 15, 2008
Received: August 7, 2008

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Article

Synthesis of P,N-Heterocycles from ω-Amino-H-Phosphinates: Conformationally Restricted α-Amino Acid Analogs