STEREOSELECTIVE CHAIN EXTENSION OF (R,R)-1,2-DICYCLOHEXYLETHANE-1,2-DIOL OR (S,S)-1,2-DICYCLOHEXYLETHANE-1,2-DIOL TRITYLOXYMETHYLBORONATE TO COMPOUNDS HAVING 3 STEREOGENIC CENTERS

Authors
MATTESON DS YANG JJ
Citation
Ds. Matteson et Jj. Yang, STEREOSELECTIVE CHAIN EXTENSION OF (R,R)-1,2-DICYCLOHEXYLETHANE-1,2-DIOL OR (S,S)-1,2-DICYCLOHEXYLETHANE-1,2-DIOL TRITYLOXYMETHYLBORONATE TO COMPOUNDS HAVING 3 STEREOGENIC CENTERS, Tetrahedron : asymmetry, 8(23), 1997, pp. 3855-3861
Citations number
14
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
8
Issue
23
Year of publication
1997
Pages
3855 - 3861
Database
ISI
SICI code
0957-4166(1997)8:23<3855:SCEO(>2.0.ZU;2-7
Abstract
The highly diastereoselective chain extension of (R)- or (S)-(R,R*)-1 ,2-dicyclohexylethane-1,2-diol ('DICHED') boronic esters has been appl ied to enantiomerically pure DICHED [(trityloxy)methyl]boronate to pro vide possible precursors of kainic acid. A five carbon chain has been assembled having the two critical stereogenic centers in the correct a bsolute configurations, with the third stereogenic center in a single absolute configuration potentially convertible to the correct amino ac id diastereomer. However, peroxidic deboronation of the potential sec- kainic acid precursor took an unexpected course. (C) 1997 Published by Elsevier Science Ltd. All rights reserved.