Enantioselective synthesis of allenyl carbinols by the CBS reduction in nitroethane: dramatic solvent effect for reactivity and enantioselectivity.
Dramatic solvent effect of nitroethane was observed in the catalytic asymmetric reductions of allenyl ketones and alpha,beta-ynones using the oxazaborolidine cayalyst to yield the corresponding alcohols in high levels of enantioselectivity.
Yu
Chan-Mo
CM
Department of Chemistry and Lab for Metal-Catalysed Reactions, Sungkyunkwan University, Suwon, 440-746, Korea. cmyu@chem.skku.ac.kr
Kim
Chunsan
C
Kweon
Jae-Hong
JH
D000498:Allyl Compounds / Q000138:chemical synthesis*; D001372:Aza Compounds / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D004980:Ethane / Q000031:analogs & derivatives* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D000432:Methanol / Q000138:chemical synthesis*; D015394:Molecular Structure; D009595:Nitroparaffins / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D000498:Allyl Compounds; D001372:Aza Compounds; D001896:Boron Compounds; D007659:Ketones; D009595:Nitroparaffins; C496870:methoxy oxazaborolidine; C014705:nitroethane; D004980:Ethane; D000432:Methanol