Cycloaddition of chloroketene to imines: synthesis of cis and trans 3-chloro-2-azetidinones
✍ Scribed by David A. Nelson
- Publisher
- Elsevier Science
- Year
- 1971
- Tongue
- French
- Weight
- 181 KB
- Volume
- 12
- Category
- Article
- ISSN
- 0040-4039
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## Abstract Zinc enolates of phenyl‐ and __trans__‐styryl‐acetic acid methyl ester react with excellent diastereoselectivety and good enantioselectivety (e.e. 64 to 91.5%) with imines in high yields to __trans__‐2‐azetidinones. The corresponding lithium enolates reacted with much lower selectivity
In the cycloaddition of chlorosulfonyl isocyanate (CSI) to olefins, Graf 182 envisioned a two-step mechanism involving the initial formation of a 'dipolar adduct' &which could stabilize itself through closure to the four-membered%and/or \*proton shift toA. Similarly,