96863-69-3Relevant academic research and scientific papers
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.
Direct, practical, and powerful crossed aldol additions between ketones and ketones or aldehydes utilizing environmentally benign TiCl4-Bu3N reagent
Tanabe, Yoo,Matsumoto, Noriaki,Higashi, Takahiro,Misaki, Tomonori,Itoh, Tomotaka,Yamamoto, Misako,Mitarai, Kumi,Nishii, Yoshinori
, p. 8269 - 8280 (2007/10/03)
An efficient TiCl4-Bu3N - (cat. TMSCl)-promoted aldol addition between ketones and ketones or aldehydes was performed. This environmentally benign method is advantageous from a green chemical viewpoint with regard to yield, substrate
Catalytic TMSCl promoted powerful aldol addition and Claisen condensation mediated by TiCl4/Bu3N agent: Comparison and evaluation with the Mukaiyama aldol addition
Yoshida, Yoshihiro,Matsumoto, Noriaki,Hamasaki, Ryota,Tanabe, Yoo
, p. 4227 - 4230 (2007/10/03)
TMSCl catalyst (0.05 equiv) significantly promoted the TiCl4/Bu3N-mediated direct cross aldol additions of sterically crowded ketones and α-hetero substituted ketones, and also the direct Claisen condensation between methyl esters.
Preparation of Enolates from α-Haloketones with n-BuLi, PhMgBr, or Et2Zn via Halogen-Metal Exchange Reaction
Aoki, Yoshitaka,Oshima, Koichiro,Utimoto, Kiitiro
, p. 463 - 464 (2007/10/03)
Metal-halogen exchange of α-iodoketones was performed upon treatment with n-BuLi, PhMgBr, Et2Zn or Me3Al in ether at 0 deg C to give the corresponding metal enolates which reacted with aldehydes to provide the aldol type products in good yields.
