Trialkylborane-Mediated Multicomponent Reaction for the Diastereoselective Synthesis of Anti-δ,δ-Disubstituted Homoallylic Alcohols
The trialkylborane/O2-mediated reaction of propargyl acetates having a tributylstannyl group at an alkyne terminus with aldehydes in a THF-H2O solvent system gave anti-δ,δ-disubstituted homoallylic alcohols with good to high diastereoselectivity. Intriguingly, two alkyl groups derived from trialkylborane were embedded into the reaction product. The trialkylborane plays a key role not only as a radical initiator but also as a source of alkyl radicals.
Horino, Yoshikazu,Murakami, Miki,Aimono, Ataru,Lee, Jun Hee,Abe, Hitoshi
Formations of Mixed β,β-Dihaloenals from Halogenated Secondary Alkynols
Iodine and Koser's reagent have been used in stoichiometric amounts to convert 3-bromo-1-phenylpropynol to (Z)-3-bromo-3-iodo-2-phenylpropenal in high yield.The latter is a major component of reaction mixtures of 3-iodo-1-phenylpropynol and bromine with K
Bovonsombat, Pakorn,McNelis, Edward
p. 7705 - 7708
(2007/10/02)
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