A stereoselective cyclization strategy for the preparation of γ-lactams and their use in the synthesis of α-methyl-β-proline.
Souvik Banerjee, Justin Smith, Jillian Smith, Caleb Faulkner, Douglas S Masterson
Index: J. Org. Chem. 77(23) , 10925-30, (2012)
Full Text: HTML
Abstract
A straightforward stereoselective and enantiodivergent cyclization strategy for the construction of γ-lactams is described. The cyclization strategy makes use of chiral malonic esters prepared from enantiomerically enriched monoesters of disubstituted malonic acid. The cyclization occurs with the selective displacement of a substituted benzyl alcohol as the leaving group. A Hammett study illustrates that the cyclization is under electronic control. The resulting γ-lactam can be readily converted into a novel proline analogue.
Related Compounds
Related Articles:
Diastereocontrolled synthesis of enantioenriched 3,4-disubstituted beta-prolines.
2007-01-19
[J. Org. Chem. 72 , 398, (2007)]
Beta-proline analogues as agonists at the strychnine-sensitive glycine receptor.
1992-01-24
[J. Med. Chem. 35 , 233, (1992)]
2002-06-06
[J. Med. Chem. 45(12) , 2571-8, (2002)]
2008-01-23
[J. Am. Chem. Soc. 130(3) , 875-86, (2008)]
1999-12-02
[Org. Lett. 1(11) , 1717-20, (1999)]