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A New Synthetic Approach to Novel Spiro‐β‐lactams
Author(s) -
Bhalla Aman,
Venugopalan Paloth,
Bari Shamsher S.
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600458
Subject(s) - chemistry , carbocation , lactam , lewis acids and bases , alkylation , beta lactam , halogen , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , biochemistry , antibiotics , alkyl
An operationally simple and efficient approach for the synthesis of novel spiro‐β‐lactams is described. The key reaction is a halogen‐mediated intrasulfenyl cyclization of a cis ‐3‐benzylthio‐3‐(prop‐2‐ynyloxy/‐enyloxy)‐β‐lactam procured through a Lewis acid‐mediated C‐3‐alkylation of the trans ‐3‐benzylthio‐3‐chloro‐β‐lactam carbocation equivalent. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)