Enantio- and Diastereoselective Synthesis of Highly Substituted Benzazepines by a Multicomponent Strategy Coupled with Organocatalytic and Enzymatic Procedures

详细信息    查看全文

• 作者：Lisa Moni ; Luca Banfi ; Andrea Basso ; Andrea Galatini ; Martina Spallarossa ; Renata Riva
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：January 3, 2014
• 年：2014
• 卷：79
• 期：1
• 页码：339-351
• 全文大小：502K
• ISSN：1520-6904

文摘

Enantiomerically pure 4,5-dihydro-1H-benzo[c]azepines with three contiguous stereogenic centers have been assembled by convergent strategy with a good control of diastereoselectivity. The two steps are as follows: an asymmetric organocatalytic Mannich reaction performed on Boc-imines of o-(azidomethyl)benzaldehydes, followed by a one-pot Staudinger/aza-Wittig/Ugi鈥揓oulli茅 sequence. The latter reaction represents one of the first examples of diastereoselective Ugi three-component reaction on a seven-membered cyclic imine. The o-azidomethylbenzaldehydes have been synthesized employing a simple and efficient chemoenzymatic strategy from commercially available building blocks.