65651-67-4Relevant academic research and scientific papers
Sml2-promoted reformatsky-type coupling reactions in exceptionally hindered contexts
Sparling, Brian A.,Moslin, Ryan M.,Jamison, Timothy F.
supporting information; experimental part, p. 1291 - 1294 (2009/04/08)
Highly substituted, very hindered enones were synthesized using a two-step procedure that utilizes a diiodosamarium-promoted Reformatsky-type coupling and dehydration using Martin sulfurane. Both α-chloro- and α-bromoketones were coupled with a variety of carbonyl nucleophiles to form the intermediate β-hydroxyketones, occurring with excellent diastereoselectivity, favoring the syn isomer (R1 = Me). This technique complements other methods and enables the preparation of enones outside of the scope of current olefination methodology.
METAL SALT-PROMOTED ALDOL REACTION OF SILYL ENOL ETHERS WITH ALDEHYDES
Chini, Marco,Crotti, Paolo,Gardelli, Cristina,Minutolo, Filippo,Pineschi, Mauro
, p. 673 - 676 (2007/10/02)
Simple metal salts such as lithium perchlorate and zinc triflate effectively promote aldol condensation between silyl enol ethers and aldehydes or acetals in non-protic solvents to yield the O-protected aldols in good yields. A slight preference for the syn aldol is observed when a prochiral silyl enol ether reacts with benzaldehyde, a complete syn stereoselectivity being obtained only in the case of the hindered silyl enol ether 14. The method appears to be simple and competitive with other ones previously described.
HIGHLY ENANTIOSELECTIVE ALDOL REACTION OF METHYL KETONES VIA CHIRAL STANNOUS AZAENOLATES
Narasaka, Koichi,Miwa, Tetsuo,Hayashi, Hiroki,Ohta, Masako
, p. 1399 - 1402 (2007/10/02)
Chiral 1,3-oxazolidines are readily prepared from methyl ketones and chiral norephedrine.Formation of stannous azaenolates from the oxazolidines and reaction with aldehydes followed by removal of the chiral auxiliary lead to the aldol products in high level of enantiomeric putity.
