使用3,3'-二取代联萘酚修饰的硼酸酯对醛和酮进行不对称烯丙基硼化反应。

Asymmetric allylboration of aldehydes and ketones using 3,3'-disubstitutedbinaphthol-modified boronates.

作者信息

Wu T Robert, Shen Lixin, Chong J Michael

机构信息

Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, (GWC), Department of Chemistry, University of Waterloo, Waterloo, Ontario, Canada N2L 3G1.

出版信息

Org Lett. 2004 Aug 5;6(16):2701-4. doi: 10.1021/ol0490882.

DOI:10.1021/ol0490882

PMID:15281748

Abstract

Allylboronates derived from 3,3'-disubstituted 2,2'-binaphthols react with aldehydes and ketones to give the expected allylated products with up to >99:1 er. Highest selectivities were observed for aromatic ketones. The bis(trifluoromethyl) derivative is particularly outstanding in terms of reactivity, selectivity, and robustness. [reaction: see text]

摘要

源自3,3'-二取代2,2'-联萘酚的烯丙基硼酸酯与醛和酮反应，生成预期的烯丙基化产物，对映体过量比高达>99:1。对芳香酮观察到最高的选择性。双（三氟甲基）衍生物在反应性、选择性和稳定性方面尤为突出。[反应：见正文]