Deprotonation of N-benzyl-3-phenylselenylpyrrol-2(5H)-one 3 and furan-2(5H)-one 4 and reaction with aldehydes affords regioselectively 5-(1'-hydroxy)-gamma-butyrolactones and the aza-analogous butyrolactams with good diastereoisomeric excesses. The presence of Lewis acids enhances the diastereoisomeric ratios. This methodology is an alternative to Lewis acid mediated silyloxydiene condensation. (C) 2000 Elsevier Science Ltd. All rights reserved.
Direct vinylogous aldol addition of gamma-butyrolactones and gamma-butyrolactams / Piancatelli, Giovanni; Bella, Marco; A., Squarcia; C., Trolli. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 41:(2000), pp. 3669-3672. [10.1016/s0040-4039(00)00439-1]
Direct vinylogous aldol addition of gamma-butyrolactones and gamma-butyrolactams
PIANCATELLI, Giovanni;BELLA, Marco;
2000
Abstract
Deprotonation of N-benzyl-3-phenylselenylpyrrol-2(5H)-one 3 and furan-2(5H)-one 4 and reaction with aldehydes affords regioselectively 5-(1'-hydroxy)-gamma-butyrolactones and the aza-analogous butyrolactams with good diastereoisomeric excesses. The presence of Lewis acids enhances the diastereoisomeric ratios. This methodology is an alternative to Lewis acid mediated silyloxydiene condensation. (C) 2000 Elsevier Science Ltd. All rights reserved.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
