192064-78-1Relevant academic research and scientific papers
Stereoselective Reduction of Conjugated Homopropargylic Alcohols to (E)-Homoallylic Alcohols by Sodium Bis(2-methoxyethoxy) Aluminium Hydride
Crousse, Benoit,Alami, Mouad,Linstrumelle, Gérard
, p. 992 - 994 (1997)
The reduction of various conjugated homopropargylic alcohols with sodium bis(2-methoxyethoxy) aluminium hydride (Red-Al) in ether or THF is described. The reaction takes place cleanly and rapidly, under mild conditions, to give (E)-homoallylic alcohols st
Development of a method for the synthesis of α-substituted α,β- unsaturated lactones based on stille-type Pd-catalyzed carbonylation of (Z)- ω-iodoalkenols. An efficient and selective synthesis of (+)-hamabiwalactone B
Liao, Baiqiao,Negishi, Ei-Ichi
, p. 1241 - 1249 (2007/10/03)
Pd-Catalyzed carbonylative lactonization of (Z)-ω-iodoalkenols can be applied to synthesize α/β-unsaturated lactones containing an alkenyl or alkynyl substituent in the α position, providing a generally superior alternative to recently developed methods involving Pd-catalyzed α- substitution of α-stannyl esters, as exemplified by a highly expeditious synthesis of (+)-hamabiwalactone B.
Anti-hydroalumination of homo- and bishomopropargyl alcohols
Ma, Shengming,Liu, Fang,Negishi, Ei-Ichi
, p. 3829 - 3832 (2007/10/03)
The reaction of ω-Me3Si- or ω-Me3Ge-substituted 3-butyn-1-ol, 4-pentyn-1-ol, and their derivatives with DIBAL-H and a small trialkylalane, e.g., Me3Al or Et3Al, at 23°C gives, after iodinolysis, the corresponding (Z)-4-iodo-3-buten-1-ols and (Z)-5-iodo-4-penten-1-ols in a highly stereo- and regio-selective manner, most probably via endo-dig mode cyclic anti-hydroalumination, while treatment of ω-carbosubstituted 3-butyn-1-ols with Red-Al or LialH4 at high temperatures followed by iodinolysis can give the corresponding (Z)-4-iodo-3-buten-1-ols also in a highly regio- and stereoselective manner.
