Mase Nobuyuki, Tanaka Fujie, Barbas Carlos F
The Skaggs Institute for Chemical Biology and the Departments of Chemistry and Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Org Lett. 2003 Nov 13;5(23):4369-72. doi: 10.1021/ol035651p.
[reaction: see text] Direct catalytic aldol reactions of alpha,alpha-dialkylaldehyde donors and arylaldehyde acceptors have been performed using pyrrolidine-acetic acid bifunctional catalysts. This general and practical amine-acid combination was identified by screening catalysts using a new fluorescent detection system for carbon-carbon bond formation. Using 0.05 equiv of pyrrolidine and 0.25 equiv of acetic acid as catalyst, we obtained alpha,alpha-dialkylaldol product in 96% yield after 2 h at ambient temperature. Proline was a poor catalyst of this reaction.
[反应：见正文] 使用吡咯烷-乙酸双功能催化剂实现了α,α-二烷基醛供体与芳基醛受体的直接催化羟醛反应。通过使用一种用于碳-碳键形成的新型荧光检测系统筛选催化剂，确定了这种通用且实用的胺-酸组合。以0.05当量的吡咯烷和0.25当量的乙酸作为催化剂，在室温下反应2小时后，我们以96%的产率得到了α,α-二烷基羟醛产物。脯氨酸是该反应的不良催化剂。
