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An Easy, Stereoselective Synthesis of Hexahydroisoindol‐4‐ones under Phosphine Catalysis
Author(s) -
Duvvuru Deepti,
Betzer JeanFrançois,
Retailleau Pascal,
Frison Gilles,
Marinetti Angela
Publication year - 2011
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201000701
Subject(s) - chemistry , stereoselectivity , synthon , conjugated system , phosphine , catalysis , ring (chemistry) , pyrroline , double bond , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , polymer
A new synthetic approach to hexahydroisoindol‐4‐ones is reported, based on the formal [3+2] cyclization reaction between N ‐arylsulfonylimines and cyclic conjugated dienes, under phosphine catalysis. Key substrates are 3‐vinylcyclohex‐2‐enones with electron‐withdrawing substituents (ester, amido, cyano, phosphoryl and keto groups) on the exocyclic double bond, which afford the three‐atom synthons for the construction of the pyrroline ring. Total syn stereoselectivity is observed in these annulations. The scope of the reaction has been demonstrated and mechanistic issues are considered, based on deuteration experiments and density function theory (DFT) calculations.