通过与10-三甲基甲硅烷基-9-硼双环[3.3.2]癸烷进行不对称炔丙基化反应得到的非外消旋α-烯丙基甲醇。
Nonracemic alpha-allenyl carbinols from asymmetric propargylation with the 10-trimethylsilyl-9-borabicyclo[3.3.2]decanes.
作者信息
Hernandez Eliud, Soderquist John A
机构信息
University of Puerto Rico, Department of Chemistry, Rio Piedras, Puerto Rico 00931-3346.
出版信息
Org Lett. 2005 Nov 24;7(24):5397-400. doi: 10.1021/ol051886k.
[reaction: see text] The asymmetric propargylboration of aldehydes at -78 degrees C in <3 h with 1 provides silylated alpha-allenyl carbinols 6 (60-87%) in high ee (94% to >98% ee). The reagents 1 are easily prepared in both enantiomeric forms with a simple Grignard procedure and air-stable borinate complexes 2. The ozonolysis of 6 proceeds smoothly through an acylsilane intermediate to give a TMS ester, which is hydrolyzed to the alpha-hydroxy acid quantitatively with water.
[反应：见正文] 在-78℃下，醛与1在<3小时内进行不对称炔丙基硼氢化反应，可提供硅烷化的α-烯丙基甲醇6（产率60 - 87%），对映体过量值高（ee为94%至>98%）。试剂1可通过简单的格氏反应步骤以及空气稳定的硼酸酯配合物2轻松制备成两种对映体形式。6的臭氧分解通过酰基硅烷中间体顺利进行，得到三甲基硅基酯，该酯用水定量水解为α-羟基酸。
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