A new method for the synthesis of 2-cyclopenten-1-one-5-carboxylic ester derivatives via Rh-2(OAc)(4)-mediated intramolecular C-H insertion reaction of 4Z-beta-vinyl-alpha-diazo beta-ketoesters

作者：Deng, GS^*; Xu, BH; Wang, JB

来源：Tetrahedron, 2005, 61(45): 10811-10817.

DOI：10.1016/j.tet.2005.05.106

• synthesis
• insertion
• 2-cyclopenten-1-one-5-carboxylic ester derivatives
• 4Z-beta-vinyl-alpha-diazo beta-ketoesters

2-Cyclopenten-1-one-5-carboxylic ester derivatives 14 are synthesized in a four- step-reaction sequence starting from alkynyl aldehydes 9 via 4Z-beta-vinyl-alpha-diazo beta-ketoesters intermediate 8. The synthetic method for 8 is described. When the delta substituent is an alkyl group, Rh(Il)-mediated decomposition of the diazo compounds 8 led to an intramolecular C-H insertion to afford 2-cyclopenten-1-one-5-carboxylic ester derivatives 14 in high yields. When the delta substituent is an aryl group, 2-hydroxynaphthoate 15 is obtained exclusively. In both cases, no Wolff rearrangement product was observed.

• 出版日期2005-11-7
• 单位北京大学; 湖南师范大学