Effect of temperature on the enantioselectivity in the   oxazaborolidine-catalyzed asymmetric reduction of ketones. Noncatalytic   borane reduction, a nonneglectable factor in the reduction system

doi:10.1021/jo035203v

CORC > 北京大学 > 化学与分子工程学院

	Effect of temperature on the enantioselectivity in the oxazaborolidine-catalyzed asymmetric reduction of ketones. Noncatalytic borane reduction, a nonneglectable factor in the reduction system
	Xu, JX ; Wei, TZ ; Zhang, QH
刊名	journal of organic chemistry
	2003
关键词	LINEAR SECONDARY ALCOHOLS PROCHIRAL KETONES CHIRAL OXAZABOROLIDINES CARBONYL-COMPOUNDS AMINO-ALCOHOLS MECHANISM ACID ACETOPHENONE SELECTIVITY ADDUCTS
DOI	10.1021/jo035203v
英文摘要	The effect of temperature on the enantioselectivity of the oxazaborolidine-catalyzed asymmetric borane reduction of ketones has been investigated carefully using alkyl aryl ketones with a variety of functional groups and a B-methoxyoxazaborolidine derived from trimethyl borate and (S)-alpha,alpha-diphenylprolinol as a catalyst. The reductions were carried out over a range of temperatures in THIP and toluene with or without the catalyst. The reductive rates increase along with increasing reaction temperature with or without the catalyst by determining the conversion of the ketones to alcohols by GC analysis. However, the rates of the catalytic reductions increase faster than those without the catalyst. The results indicate that the noncatalytic borane reduction is an important factor to the enantioselectivity in the reduction. The highest enantioselectivities were usually obtained between 20 and 30 degreesC in the asymmetric reduction.; Chemistry, Organic; SCI(E); EI; PubMed; 52; ARTICLE; 26; 10146-10151; 68
语种	英语
内容类型	期刊论文
源URL	[http://ir.pku.edu.cn/handle/20.500.11897/150274]
专题	化学与分子工程学院
推荐引用方式 GB/T 7714	Xu, JX,Wei, TZ,Zhang, QH. Effect of temperature on the enantioselectivity in the oxazaborolidine-catalyzed asymmetric reduction of ketones. Noncatalytic borane reduction, a nonneglectable factor in the reduction system[J]. journal of organic chemistry,2003.
APA	Xu, JX,Wei, TZ,&Zhang, QH.(2003).Effect of temperature on the enantioselectivity in the oxazaborolidine-catalyzed asymmetric reduction of ketones. Noncatalytic borane reduction, a nonneglectable factor in the reduction system.journal of organic chemistry.
MLA	Xu, JX,et al."Effect of temperature on the enantioselectivity in the oxazaborolidine-catalyzed asymmetric reduction of ketones. Noncatalytic borane reduction, a nonneglectable factor in the reduction system".journal of organic chemistry (2003).