ORGN 80 |
Simple thiazocine-2-acetic acid derivatives via ring-closing metathesis (RCM)
| Dallas K. Bates, Xiaofen Li, and Parag V. Jog. Department of Chemistry, Michigan Technological University, 1400 Townsend Drive, Houghton, MI 49931 |
| A new protocol for synthesis of 2-heterocylylacetic acid derivatives involving conjugate addition of allyl mercaptan to an acrylate containing a tethered olefinic site followed by RCM is described. Use of the sulfoxide oxidation state as a protecting group for sulfides inert to RCM is demonstrated also. For example, sulfide (2) was inert to Grubbs’ second generation catalyst. However, oxidation to sulfoxide (3) followed by RCM provided thiazocine 6. Deprotection (deoxygenation) to 5 was accomplished using Lawesson’s reagent. Sulfones 4 provided thiazocines 7 in excellent yield.  |
| |
|
New Reactions and Methodology, Metal-Mediated Reactions, Heterocycles and Aromatics
8:00 PM-10:00 PM, Sunday, March 28, 2004 Anaheim Convention Center -- Hall A, Poster
Division of Organic Chemistry
The 227th ACS National Meeting, Anaheim, CA, March 28-April 1, 2004
|