PRODUCTION OF HOMOALLYLAMINE

摘要

PROBLEM TO BE SOLVED: To obtain a homoallylamine which is useful as a synthetic intermediate in alkaloid synthesis by addition reaction of an allyl reagent to an optically active N-sulfinylimine. SOLUTION: An allyl Grignard reagent, boron trifluoride ether complex or cerium chloride and an allyl Grignard reagent are allowed to react with a compound of formula I to prepare a compound of formula II. The kinds of metal in the allylation reagent and the reaction solvents are properly selected to arbitrarily obtain both diastereomers of corresponding homoallylamine in high yield and in high selectivity of 98%de at maximum. This indolizidine 223AB is isolated from the venom components of arrow toxin frog and has an activity of an antagonist in nicotine receptor channel and is one kind of alkaloid bearing N-containing 5 or 6-membered ring structure.