82105-30-4Relevant academic research and scientific papers
Direct use of esters in the Mukaiyama aldol reaction: A powerful and convenient alternative to aldehydes
Inamoto, Yoshihiro,Nishimoto, Yoshihiro,Yasuda, Makoto,Baba, Akio
, p. 1168 - 1171 (2012/04/04)
An indium triiodide catalyst promoted the direct transformation from esters to β-hydroxycarbonyl compounds using hydrosilanes and silyl enolates by a one-stage process. Various esters were applicable, and the high chemoselectivity of this system brings compatibility to many functional groups: alkenyl, alkynyl, chloro, and hydroxy.
Stereoselective crossed aldol reaction via boron enolates generated from α-iodo ketones and 9-borabicyclo[3.3.1]nonane
Mukaiyama, Teruaki,Takuwa, Tomofumi,Yamane, Keiko,Imachi, Shouhei
, p. 813 - 823 (2007/10/03)
Boron enolates were in situ-generated reductively by treating various α-iodo ketones such as 2-iodo-1-phenylpropan-1-one, 2-iodo-1-(4-methoxyphenyl)propan-1-one, 2-iodopentan-3-one, 2-iodo-2-methyl-1-phenylpropan-1-one, 3,4-dihydro-2-iodo-1(2H)-naphthalenone, 2-iodo-1-phenylethan-1-one and 1-iodo-4-phenylbutan-2-one with 9-borabicyclo[3.3.1]nonane (9-BBN). Aldols were produced in good yields with good to high diastereoselectivities by subsequent reaction of boron enolates thus formed with various aldehydes. Several boron enolates derived from α-iodo ketones and pinacolatoborane were successfully isolated by distillation, though the yields were rather moderate.
Organometallic reactions in aqueous media - Bismuth-mediated crossed aldol type reactions
Lee, Yoon Joo,Chan, Tak Hang
, p. 1406 - 1412 (2007/10/03)
Bismuth metal, upon activation by zinc fluoride, can effect the crossed aldol reaction between α-bromocarbonyl compounds and aldehydes in aqueous media. The reaction was found to be regiospecific and syndiastereoselective.
A NEW METHOD FOR THE REGIO- AND STEREOSELECTIVE SYNTHESIS OF ALDOLS FROM α-BROMOKETONE AND CARBONYL COMPOUNDS BY USING METALLIC TIN
Harada, Taira,Mukayiama, Teruaki
, p. 467 - 470 (2007/10/02)
Tin(II) enolates, generated in situ by the oxidative addition of α-bromoketones to metallic tin, react with a variety of carbonyl compounds under mild conditions to give the corresponding aldols in good yields.In the case of reactions of the enolate resul
