A new catalytic enantioselective reducing reagent system from (-)-α,α-diphenylpyrrolidinemethanol and 9-borabicyclo[3.3.1]nonane, especially effective for hindered and substituted aralkylketones
A new catalytic enantioselective reducing reagent system from (-)-α,α-diphenylpyrrolidinemethanol and 9-borabicyclo[3.3.1]nonane, especially effective for hindered and substituted aralkylketones
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DOI：
10.1016/s0040-4020(01)01213-3
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发表时间：
2002-02-04
期刊：
影响因子：
2.1
通讯作者：
Brown, HC
中科院分区：
文献类型：
--
作者：
Kanth, JVB;Brown, HC
以氨基醇和二烷基硼烷为原料，合成了新的催化对映体选择性还原体系，用于前手性芳香酮的对映体选择性还原。其中，由(-)-α，α-二苯基吡咯亚甲基乙醇与9-硼双环[3.3.1]正庚烷制备的体系特别适合于这种还原。该配合物催化BH3-THF将前手性芳烷基酮还原为相应的醇，对映体选择性为82-99.2%。此外，这种催化剂对更多受阻和取代的芳烷基酮特别有效。考察了不同反应条件、不同还原剂、不同二烷基硼烷对催化还原体系的影响。(C)2002爱思唯尔科学有限公司。保留所有权利。
New catalytic enantioselective reduction systems were prepared from aminoalcohols and dialkylboranes, for the enantioselective reductions of prochiral aromatic ketones. Among these, the system prepared from (-)-alpha,alpha-diphenylpyrrolidinemethanol with 9-borabicyclo[3.3.1]nonane proved especially promising for such reductions. This complex catalyzes the reduction of prochiral aralkyl ketones to the corresponding alcohols with BH3-THF, with enantioselectivities 82-99.2%. Also, this catalyst is particularly effective for the more hindered and substituted aralkyl ketones. Various modifications in this new catalytic reduction system, such as changing reaction conditions, reducing agent and dialkylborane, were also examined. (C) 2002 Elsevier Science Ltd. All rights reserved.