@article { ISI:000319721200042, title = {CuCN-Mediated cascade cyclization of 4-(2-bromophenyl)-2-butenoates: a high-yield synthesis of substituted naphthalene amino esters}, journal = {Journal of Organic Chemistry}, volume = {78}, number = {10}, year = {2013}, month = {MAY}, pages = {5045-5050}, publisher = {AMER CHEMICAL SOC}, address = {1155 16TH ST, NW, WASHINGTON, DC 20036 USA}, abstract = {

A new method of CuCN-mediated one-pot cyclization of 4-(2-bromophenyl)-2-butenoates leading to efficient synthesis of substituted naphthalene amino esters including phenanthrene aromatic structural units is described. Deuterium labeling studies establish that this one-pot cascade cyclization proceeds through isomerization of olefin, intramolecular C-C bond cyclization, and aromatization as the key intermediates, all occurring in a single step.

}, issn = {0022-3263}, doi = {10.1021/jo400244h}, author = {Reddy, R. Santhosh and Prasad, Pragati K. and Ahuja, Brij Bhushan and Sudalai, Arumugam} } @article {45932, title = {Concise enantioselective synthesis of (2S,3S)-3-hydroxypipecolic acid via proline catalyzed alpha-aminooxylation of aldehydes and Pd-catalyzed ether directed aza-Claisen rearrangements}, journal = {Tetrahedron-Asymmetry}, volume = {26}, year = {2015}, month = {JAN }, pages = {24-28}, type = {Article}, abstract = {

An efficient approach to (2S,3S)-3-hydroxypipecolic acid with an overall yield of 10.2\% and 98\% ee starting from 1,5-pentanediol has been developed. The key steps employed in the synthesis are the D-proline catalyzed sequential alpha-aminooxylation/Horner-Wadsworth-Emmons olefination of an aldehyde and the Pd-catalyzed MOM-ether directed aza-Claisen rearrangement of an allylic trichloroacetimidate. (C) 2014 Elsevier Ltd. All rights reserved.

}, issn = {0957-4166}, doi = {10.1016/j.tetasy.2014.11.010}, author = {Ahuja, Brij Bhushan and Sudalai, Arumugam} } @article { ISI:000354794500012, title = {Cu-catalyzed debrominative cyanation of gem-dibromoolefins: a facile access to alpha,beta-unsaturated nitriles}, journal = {Organic \& Biomolecular Chemistry}, volume = {13}, number = {21}, year = {2015}, month = {APR}, pages = {5918-5923}, publisher = {ROYAL SOC CHEMISTRY}, address = {THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND}, abstract = {

An efficient catalytic route for the synthesis of alpha,beta-unsaturated nitriles from easily accessible gem-dibromoolefins has been developed. The method utilized inexpensive reagents such as Cu2O as a catalyst, L-proline as a ligand and NaCN as a cyanide source to afford alpha,beta-unsaturated nitriles in high yields (62-86\%). A deuterium exchange study has shown that one of the bromide atoms of gem-dibromoolefins exchanges with cyanide while the other with a deuterium atom.

}, issn = {1477-0520}, doi = {10.1039/c5ob00394f}, author = {Ahuja, Brij Bhushan and Sudalai, Arumugam} }