In:
Advanced Synthesis & Catalysis, Wiley, Vol. 350, No. 14-15 ( 2008-10-06), p. 2279-2285
Abstract:
An operationally simple four‐step procedure for the solid‐phase synthesis of chiral (3 S ,4 S )‐1,3,4,4‐tetrasubstituted β‐lactams is described. The key step for the four‐membered ring formation consisted in the enantioselective phosphazene base‐assisted cyclization of resin‐bound N ‐(alkyl)‐ N ‐[( S )‐2‐chloropropionyl]amino acid derivatives. A low‐epimerization process during the incorporation of the 2 S ‐chloropropionyl moiety into the N ‐alkylamino acid resins was crucial for the final stereochemical outcome, since the 3,4‐stereochemistry was exclusively dictated by the configuration of this moiety. To evaluate the scope of this procedure a small library of quaternary, highly functionalized β‐lactams has been generated.
Type of Medium:
Online Resource
ISSN:
1615-4150
,
1615-4169
DOI:
10.1002/adsc.v350:14/15
DOI:
10.1002/adsc.200800432
Language:
English
Publisher:
Wiley
Publication Date:
2008
detail.hit.zdb_id:
2041384-1
detail.hit.zdb_id:
2033084-4
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