Cycloaddition chemistry of 1,3- and 2,3-bis(phenylsulfonyl)-1,3-dienes with enamines and ynamines
โ Scribed by Padwa, Albert; Gareau, Yves; Harrison, Brian; Rodriguez, Augusto
- Book ID
- 120356747
- Publisher
- American Chemical Society
- Year
- 1992
- Tongue
- English
- Weight
- 806 KB
- Volume
- 57
- Category
- Article
- ISSN
- 0022-3263
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๐ SIMILAR VOLUMES
Reaction of 1-indolylmagnesium iodidelo with the appropriate sulfonyldiene in benzene-ether (1: 1) at 0 "C resulted in a cycloaddition and after workup the teaahydrocarbazole product was isolated. Results from the reaction of a few 2-phenylsulfonyl 1,3-dienes are given in Table 1. In all cases only
Z-Phenylsulfonyl 1,3-dienes underwent diastereoselective inverse electron demand Diels-Alder reactions with enamines (up to 73% de) and enol ethers (up to 50% de). 2-Phenylsulfonyl 1,3-dienes are useful building blocks in organic synthesis,'" and several methods for their preparation have recently b
## Abstract The cycloaddition of organic azides with some conjugated enamines of the 2โaminoโ1,3โdiene, 1โaminoโ1,3โdiene, and 2โaminobutโ1โenโ3โyne type is investigated. The 2โmorpholinobutaโ1,3โdiene **1** undergoes regioselective [3+2] cycloaddition with several electrophilic azides RN~3~ **2**