NDLI: A Comparative Study of the Relative Stability of Representative Chiral and Achiral Boronic Esters Employing Transesterification

Content Provider	Springer Nature Link
Author	Roy, Chandra D. Brown, Herbert C.
Copyright Year	2007
Abstract	A comparative study of the transesterification of five representative chiral and achiral boronic esters with various structurally modified diols was undertaken to qualitatively understand the factors influencing the relative stability of these boronic esters. Several factors such as chelation, conformation, steric bulk of the substituents, size of the heterocycle, and entropy influence the relative rate of transesterification as well as the stability of the boronic esters. Amongst these boronic esters, pinanediol phenylboronic ester was found to be the most stable boronic ester whereas DIPT boronic ester appeared to be thermodynamically the least stable one. The transesterification with sterically hindered diols was observed to be relatively slow, but afforded thermodynamically more stable boronic esters. Boronic esters derived from cis-cyclopentanediols and the bicyclo[2.2.1]heptane-exo,exo-2,3-diols are relatively more stable. This study not only presents the qualitative picture of relative stability of various boronic esters, but also provides helpful hints regarding the possible recovery of chiral auxiliaries. Many C 2-symmetric chiral auxiliaries, such as 2,3-butanediol, 2,4-pentanediol, DIPT, and cis-cyclohexane-1,2-diol, can be retrieved by simple transesterification of the corresponding boronic esters with commercial inexpensive diols, such as pinacol, 1,3-propanediol, and neopentyl glycol.
Starting Page	879
Ending Page	887
Page Count	9
File Format	PDF
ISSN	00269247
Journal	Monatshefte für Chemie - Chemical Monthly
Volume Number	138
Issue Number	9
e-ISSN	14344475
Language	English
Publisher	Springer-Verlag
Publisher Date	2007-06-29
Publisher Place	Vienna
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Chemistry/Food Science Analytical Chemistry Inorganic Chemistry Organic Chemistry Physical Chemistry Theoretical and Computational Chemistry
Content Type	Text
Resource Type	Article
Subject	Chemistry

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