Tetrahedron Asymmetry p. 1741 - 1749 (1997)
Update date:2022-08-17
Topics:
Jezewski, Artur
Chajewska, Katarzyna
Wielogorski, Zbigniew
Jurczak, Janusz
The asymmetric ene reaction of N-glyoxyloyl-(2R)-bornane-10,2-sultam 2 and its hemiacetal 3 with 1-pentene 4 and 1-hexene 5 in the presence of Lewis acids is reported. All the ene reactions studied led to diastereoisomeric mixtures of olefins 6 and 7 or 8 and 9, with predominance of products of the (S) absolute configuration on the newly formed stereogenic center. The absolute configuration (via X-ray analysis of 6 and chemical correlation) and the extent of asymmetric induction were established. Stereochemical models are proposed.
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