Novel asymmetric phenylselenium-induced lactamizations of olefinic amides: stereoselective routes to alpha- and beta-amino acids
SCIE
SCOPUS
- Title
- Novel asymmetric phenylselenium-induced lactamizations of olefinic amides: stereoselective routes to alpha- and beta-amino acids
- Authors
- Chung, SK; Jeong, TH; Kang, DH
- Date Issued
- 1998-03-07
- Publisher
- ROYAL SOC CHEMISTRY
- Abstract
- Organoselenium-induced cyclofunctionalization of the (S)-N-(alpha,beta-unsaturated) acylprolinamides 1, 7 and 14 has been found to produce the 7-membered bislactam products 2 and 15, or the 6-membered phenylselenolactam products 8 and 9 depending on the substitution pattern of the enone moiety of the starting material. The structural identities and stereochemistry of the cyclized products have been determined by X-ray diffraction, and the diastereoselectivity in the formation of the 7-membered ring bislactam product was found to be 91.6% de. The mechanism of the cyclolactamization is discussed.
- Keywords
- ORGANOSELENIUM-INDUCED CYCLIZATION; NITROGEN-HETEROCYCLES; LACTAMS; OXIMES
- URI
- https://oasis.postech.ac.kr/handle/2014.oak/20838
- DOI
- 10.1039/a705390h
- ISSN
- 0300-922X
- Article Type
- Article
- Citation
- JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, no. 5, page. 969 - 976, 1998-03-07
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