Abstract
The reaction of crotyltrialkylstannanes ( 1) with aldehydes in the presence of BF 3,OEt 2, produces the corresponding erythro homoallyl alcohols ( 2) predominantly regardless of the geometry of the double bond. Further, the Lewis acid mediated reaction exhibits the enhanced Cram selectivity in comparison with other allylic organometallic reactions which proceed in the absence of Lewis acids. Use of AlCl 3-i-PrOH as the Lewis acid entirely changes the reaction course; the linear adduct ( 12) is produced rather than the branched adduct ( 13). The reaction of 1-BF 3,OEt 2 system is applied to the short and stereoselective synthesis of the (±) Prelog-Djerassi lactonic acid ( 16) and (-) verrucarinolactone ( 19).
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
