Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 18, Pages 7438-7448Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo201209x
Keywords
-
Categories
Funding
- Institut de Chimie des Substances Naturelles
- COST Action [D40]
Ask authors/readers for more resources
Catalytic intramolecular alkene aziridination of sulfamate is an emerging methodology for the asymmetric synthesis of chiral functionalized amines involving the formation of bicyclic aziridines. This study demonstrates the ability of the latter to undergo ring-opening with various carbon nucleophiles: Grignard reagents, lithium salts of terminal alkynes, dithiane, malonate. These S(N)2-type reactions occur with high levels of regio- and chemoselectivity to generally afford seven-membered cyclic sulfamidates in good yields. Carbon nucleophiles have also been found to react with these sulfamidates provided that the sulfamate ester has been previously activated by introduction of a tosyl substituent on the NH group. The versatility of this strategy has been illustrated with the syntheses of spisulosine and its fluor analogue.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available