Transformation of an optically active decahydro-6-isoquinolone scaffold: perfect Felkin-Anh diastereoselectivity.
Diastereomerically and enantiomerically pure decahydro-6-isoquinolone derivative 7 (>99% de, 97% ee) was obtained from the Michael addition product 3. Interestingly, aldehyde 7 reacted with a number of different Grignard reagents to give the secondary alcohols 9 in good yields as single diastereomers. This result can be explained by taking the Felkin-Anh model into account.
Christoffers
Jens
J
Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart, Germany. jchr@po.uni-stuttgart.de
Scharl
Heiko
H
Frey
Wolfgang
W
Baro
Angelika
A