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Synlett 1995; 1995(8): 847-849
DOI: 10.1055/s-1995-5103
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Highly Regioselective Silylation of α,β-Dihydroxyphosphonates: An Application to Stereoselective Synthesis of α-Amino-β-hydroxyphosphonic Acid Derivatives

Tsutomu Yokomatsu, Kenji Suemune, Takehiro Yamagishi, Shiroshi Shibuya*
  • *School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-03, Japan
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Publikationsdatum:
31. Dezember 2000 (online)

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tert-Butyldimethylsilylation of threo-α,β-dihydroxyphosphonates 1 and 6a,c-e proceeded with high degree of regioselectivity to give the corresponding β-siloxy derivatives. As an application of these findings, a stereocontrolled synthesis of erythro-α-amino-β-siloxyphosphonate 9 was achieved in an optically active form from α,β-dihydroxyphosphonate 1.

α,β-dihydroxyphosphonates - regioselective silylation - α-amino-β-hydroxyphosphonates