通过 2-硝糖的串联[4+1]环加成和重排反应，轻松合成糖基整合的异恶唑啉。

Facile synthesis of carbohydrate-integrated isoxazolines through tandem [4+1] cycloaddition and rearrangement of 2-nitroglycals.

机构信息

Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371.

出版信息

Chem Commun (Camb). 2011 Aug 14;47(30):8676-8. doi: 10.1039/c1cc12327k. Epub 2011 Jun 29.

DOI:10.1039/c1cc12327k

PMID:21717033

Abstract

Carbohydrate-integrated isoxazolines were synthesized from 2-nitroglycals and sulfur ylides, with the aid of 1-phenylthiourea catalyst. The reactions proceeded via [4+1] annulations and upon subsequent rearrangement, afforded the corresponding isoxazolines in high yields with excellent diastereoselectivities (up to 95% de).

摘要

碳水化合物整合异恶唑啉是由 2-硝糖和硫叶立德在 1-苯硫脲催化剂的辅助下合成的。反应通过[4+1]环加成和随后的重排进行，以高收率和优异的非对映选择性（高达 95% de）得到相应的异恶唑啉。