Stereochemical Aspects of Aldehyde Additions to Cyclohex-2-Enylstannanes
Keyword(s):
Cyclohex-2-enylation of aldehydes, mediated with boron trifluoride etherate, involves γ-equatorial approach of the presumed aldehyde-Lewis acid adduct (RCHO-BF3), irrespective of starting stannane stereochemistry. Marginal threo selectivity characterizes homoallyl alcohol formation from benzaldehyde, whereas alkanals react with high erythro selectivity, so that 1-(1′-hydroxyalkyl)cyclohex-2-enes in this diastereomeric form are available based on allyltin chemistry.
Keyword(s):
1996 ◽
Vol 10
(2)
◽
pp. 95-96
◽
Keyword(s):
Keyword(s):
1998 ◽
Vol 21
(3)
◽
pp. 353-356
◽
Keyword(s):