Asymmetric synthesis of beta- and gamma-amidophosphonates by Diels-Alder reaction using chiral aminodiene: theoretical and experimental study of the facial selectivity of chiral N-dienyl lactam

Robiette, Raphaël;Marchand-Brynaert, Jacqueline
(2001) Royal Chemical Society. Journal. Perkin Transactions 2 — n° 11, p. 2155-2158 (2001)

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Abstract
Asymmetric [4 + 2] cycloaddition of optically pure 1-aminodiene 1 onto substituted phosphonodienophiles 2 and 4 provided respectively chiral beta- and gamma -amidophosphonocyclohexenes with good selectivities. The absolute stereochemistry of the major diastereoisomer was experimentally proved by NMR experiments and the facial selectivity of diene 1 is discussed on the basis of ab initio calculations.
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Robiette, R., & Marchand-Brynaert, J. (2001). Asymmetric synthesis of beta- and gamma-amidophosphonates by Diels-Alder reaction using chiral aminodiene: theoretical and experimental study of the facial selectivity of chiral N-dienyl lactam. Royal Chemical Society. Journal. Perkin Transactions 2, 11, 2155-2158. https://doi.org/10.1039/b105070m (Original work published 2001)