通过β-甲代烯丙基-10-(三甲基硅基和苯基)-9-硼双环[3.3.2]癸烷实现二级和三级碳醇的不对称合成。
Asymmetric synthesis of 2 degrees- and 3 degrees-Carbinols via B-methallyl-10-(TMS and Ph)-9-borabicyclo[3.3.2]decanes.
作者信息
Roman José G, Soderquist John A
机构信息
Department of Chemistry, University of Puerto Rico, Rio Piedras, Puerto Rico 00931-3346.
出版信息
J Org Chem. 2007 Dec 7;72(25):9772-5. doi: 10.1021/jo701633k. Epub 2007 Nov 14.
Abstract
Simple Grignard procedures provide methallylboranes 1a and 1b in enantiomerically pure form from air-stable precursors in 98% and 95% yields, respectively. These reagents add smoothly to aldehydes and methyl ketones, respectively, providing branched 2 degrees- (6, 69-89%, 94-99% ee) and 3 degrees- (10, 71-87%, 74-96% ee) homoallylic alcohols.
摘要
简单的格氏反应步骤分别以98%和95%的产率从空气稳定的前体中得到对映体纯形式的甲基烯丙基硼烷1a和1b。这些试剂分别顺利地加成到醛和甲基酮上，得到支链型二级（6，产率69 - 89%，对映体过量94 - 99%）和三级（10，产率71 - 87%，对映体过量74 - 96%）高烯丙醇。
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