@article { ISI:000227267300021, title = {Synthesis of cis bis-beta-lactams via Staudinger cycloaddition reaction using C-2-symmetric 1,2-diamines}, journal = {Tetrahedron}, volume = {61}, number = {9}, year = {2005}, month = {FEB}, pages = {2441-2451}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

An efficient stereoselective synthesis of bis-beta-lactams via cycloaddition reaction (Staudinger reaction) of ketenes with bisimines derived from C-2-symmetric 1, 2-diamines is described. The reaction provided diastereomeric mixture of meso and C-2-symmetric cis-bis-beta-lactams with higher selectivity for meso-bis-beta-lactams. (C) 2005 Elsevier Ltd. All rights reserved.

}, keywords = {imines, ketenes, Staudinger cyclo-addition reaction, stereoselective synthesis}, issn = {0040-4020}, doi = {10.1016/j.tet.2005.01.031}, author = {Shaikh, A. L. and Puranik, Vedavati G. and Deshmukh, A. R. A. S.} } @article { ISI:000237126200040, title = {4-Formylazetidin-2-ones, synthon for the synthesis of (2R,3S) and (2S,3R)-3-amino-2-hydroxydecanoic acid (AHDA)}, journal = {Tetrahedron}, volume = {62}, number = {18}, year = {2006}, month = {MAY}, pages = {4615-4621}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, type = {Article}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

An efficient synthesis of 3-amino-2-hydroxydecanoic acid (AHDA), a nonproteinogenic amino acid, using enantiopure 3-benzyloxy-4-formylazetidin-2-one as a building block is described. Both the enantiomers of AHDA have been synthesized from the corresponding enantiomer of 3-benzyloxy-4-formylazetidin-2-one in good yield and optical purity. (c) 2006 Published by Elsevier Ltd.

}, keywords = {Amino acids, azetidin-2-ones, Staudinger reaction, stereoselective synthesis, Wittig reaction}, issn = {0040-4020}, doi = {10.1016/j.tet.2006.01.082}, author = {Shirode, N. M. and Deshmukh, A. R. A. S.} } @article { ISI:000239289800036, title = {Gamma-heteroatom directed stereocontrolled staudinger cycloaddition reaction of vinylketenes and imines}, journal = {Tetrahedron Letters}, volume = {47}, number = {33}, year = {2006}, month = {AUG}, pages = {5993-5996}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, type = {Article}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

Vinylketenes possessing a gamma-heteroatom, on Staudinger cycloaddition reaction with imines gave trans-3-vinyl-beta-lactams in very good yields. The vinyl side chain stereoselectively adopts the Z-configuration in the transition state to stabilize the vinylketene and produces, exclusively, trans-3-vinyl-beta-lactams. (c) 2006 Elsevier Ltd. All rights reserved.

}, keywords = {imines, Staudinger reaction, stereoselective synthesis, vinylketenes}, issn = {0040-4039}, doi = {10.1016/j.tetlet.2006.05.189}, author = {Shaikh, Aarif L. and Puranik, Vedavati G. and Deshmukh, A. R. A. S.} } @article { ISI:000252091800019, title = {Stereoselective synthesis of spiro-beta-lactams using D-(+)-glucose derived chiral pool: remarkable influence of the torquoelectronic effect}, journal = {Tetrahedron}, volume = {63}, number = {37}, year = {2007}, month = {SEP}, pages = {9179-9187}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, type = {Article}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

Diastereoselective synthesis of spiro-beta-lactams via [2+2] cycloaddition reaction of imines and chiral ketenes is described. The chiral ketene was prepared from commercially available, inexpensive D-glucose. Although, theoretically four diastereomers are possible, the reaction yielded only two diastereomers stereoselectively in good to moderate yields. The stereochemical outcome of the reaction was in accordance with the torquoelectronic model. (c) 2007 Elsevier Ltd. All rights reserved.

}, keywords = {imines, ketenes, spiro-beta-lactams, Staudinger reaction, stereoselective synthesis}, issn = {0040-4020}, doi = {10.1016/j.tet.2007.06.073}, author = {Chincholkar, Pinak M. and Puranik, Vedavati G. and Deshmukh, A. R. A. S.} }