Stereoselective Synthesis of Novel 4,5-Epoxy-1,2-oxazin-6-ones and α,β-Epoxy-γ-amino Acids from β-Lithiated Oxazolinyloxiranes and Nitrones

A stereoselective synthesis of 9,10-epoxy-1,6-dioxa-4,7-diazaspiro[4,5]decanes has been developed on the basis of the addition of β-lithiated oxazolinyloxiranes to nitrones. Conversion of these spirocyclic derivatives into 4,5-epoxy-1,2-oxazin-6-ones and successively into α,β-epoxy-γ-amino acids, α-hydroxy-γ-amino acids, and γ-butyrolactams is described.

[1]  P. Wipf,et al.  Three-component synthesis of alpha,beta-cyclopropyl-gamma-amino acids. , 2005, Organic letters.

[2]  D. Seebach,et al.  The World of β‐ and γ‐Peptides Comprised of Homologated Proteinogenic Amino Acids and Other Components , 2004 .

[3]  L. Degennaro,et al.  Oxazolinyloxiranyllithium-mediated synthesis of highly strained heterocyclic compounds , 2003 .

[4]  P. Balaram,et al.  Alpha-gamma hybrid peptides that contain the conformationally constrained gabapentin residue: characterization of mimetics of chain reversals. , 2003, Chemistry.

[5]  L. Degennaro,et al.  Oxazolinyloxiranyllithium-mediated stereoselective synthesis of alpha-epoxy-beta-amino acids. , 2003, Organic Letters.

[6]  O. Reiser,et al.  Synthesis and applications of beta-aminocarboxylic acids containing a cyclopropane ring. , 2003, Chemical reviews.

[7]  L. Degennaro,et al.  On the Addition of Lithiated 2-Alkyl- and 2-(Chloroalkyl)-4,5-dihydro-1,3-oxazoles to Nitrones − A Mechanistic Investigation , 2002 .

[8]  L. Degennaro,et al.  Stereospecific β-Lithiation of Oxazolinyloxiranes: Synthesis of α,β-Epoxy-γ-butyrolactones , 2002 .

[9]  Matthew J. Mio,et al.  A field guide to foldamers. , 2001, Chemical reviews.

[10]  S. Gellman,et al.  Parallel sheet secondary structure in gamma-peptides. , 2001, Journal of the American Chemical Society.

[11]  W. DeGrado,et al.  beta-Peptides: from structure to function. , 2001, Chemical reviews.

[12]  A. Esposito,et al.  First stereocontrolled synthesis of (S)-cleonin and related cyclopropyl-substituted amino acids. , 2001, Organic Letters.

[13]  Clayden,et al.  Dearomatizing anionic cyclization of substituted N-cumyl-N-benzyl- benzamides on treatment with LDA: synthesis of partially saturated substituted isoindolones , 2000, Organic Letters.

[14]  E. Giralt,et al.  Enantioselective synthetic approaches to cyclopropane and cyclobutane β-amino acids: synthesis and structural study of a conformationally constrained β-dipeptide , 2000 .

[15]  Hamann,et al.  A Novel Outcome of the Hydroperoxide Rearrangement. , 2000, The Journal of organic chemistry.

[16]  E. Schreiner,et al.  Inhibitors of HIV-1 proteinase containing 2-heterosubstituted 4-amino-3-hydroxy-5-phenylpentanoic acid: synthesis, enzyme inhibition, and antiviral activity. , 1994, Journal of medicinal chemistry.

[17]  S. Ram,et al.  Ammonium Formate in Organic Synthesis: A Versatile Agent in Catalytic Hydrogen Transfer Reductions , 1988 .