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Diastereoselective synthesis of 4-alkylidene-2-amino-4-phosphonobutanoic acids

✍ Scribed by M.Carmen Fernández; Marı́a Ruiz; Vicente Ojea; José M. Quintela

Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
132 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

Olefination of a-silyl-, a-phosphoryland a-stannyl-stabilised phosphonate carbanions derived from cyclo-[L-AP4-D-Val] Li + 4b-d -allow a (Z)-selective access to the a,b-substituted vinylphosphonates 7A-E that have been transformed into enantiomerically pure 4-alkylidene AP4 derivatives 12A,B and 13A,C. According to semi-empirical (PM3) calculations, the preference for like topologies in the intermediate adducts of the phosphonate addition step accounts for the highly (Z)-selective course of the 'tin-Peterson-like' olefination.

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ChemInform Abstract: Diastereoselective
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