Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 73, Issue 22, Pages 8987-8991Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo801768y
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Funding
- National Institute of General Medical Sciences
- NIH [1R01 GM067610]
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P,N-Heterocycles (3-hydroxy-1,3-azaphospholane and 3-hydroxy-1, 3-azaphosphorinane-3-oxide) are synthesized in moderate yield from readily available omega-amino-H-phosphinates and aldehydes or ketones via an intramolecular Kabachnik-Fields reaction. The products are conformationally restricted phosphinic analogs of alpha-amino acids. The multigram-scale syntheses of the H2N(CH2)(n)PO2H2 phosphinic precursors (n = 1, 2, 3) and some derivatives are also described.
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