Origin of Enantioselectivity: A Model
Study of Sharpless Epoxidation
Nabanita Paul
Abstract An enantiomerically pure substance has paramount physiological importance. Synthetic chemists aimed to produce drug molecules primarily target to synthesize pure enantiomer. Enantiomers are optically active stereoisomers so in order
to accomplish products with high enantiomeric excess, asymmetric synthesis must
be designed judiciously. Mimicking nature’s selective aptitude of biosynthesis is
always considered a crucial challenge for synthetic chemists. The main target of
drug designing is to attain skill in this specialized section. Racemization during asymmetric synthesis occasionally disappoints synthetic chemists by widely disrupting
biophysical, biochemical characteristics of the synthesized compound. Kinetic resolution, however, is able to separate two enantiomers. Among innumerable synthesis,
only a few are found to be associated with high enantiomeric excess yield. Contribution of enantioselective epoxide synthesis by Sharpless epoxidation is no less important in drug industry. Most striking feature of Sharpless epoxidation is materials used
for producing enantiospecific epoxide are inexpensive. Product spread consisting of
one predominating chiral epoxide is efficiently resolved. The current communication
is aimed to analyse Sharpless epoxidation from analytical angle of a chemist using
a model study of transition state structure using DIPT as chiral auxiliary and drives
to find the underlying basis responsible for channelizing only one enantiomer at the
suppression of other.
Keywords Diastereotopic TS · Kinetic resolution · Sharpless epoxidation
1 Introduction
The physiochemical activities are extremely specific. Almost all biochemical
responses are enzyme-controlled processes. Enzymes are chiral substances. The
degree of sensitivity is a function of chirality of the foreign moiety. In this circumstance, onus is on the synthetic chemists to synthesize enantiomerically pure
N. Paul (B)
Department of Chemistry, A.P.C Roy Govt. College, Siliguri, India
e-mail: paulnabanita367@gmail.com
© Springer Nature Singapore Pte Ltd. 2021
D. Ramkrishna et al. (eds.), Advances in Bioprocess Engineering and Technology,
Lecture Notes in Bioengineering,
https://doi.org/10.1007/978-981-15-7409-2_44
439
Study of Sharpless Epoxidation
Nabanita Paul
Abstract An enantiomerically pure substance has paramount physiological importance. Synthetic chemists aimed to produce drug molecules primarily target to synthesize pure enantiomer. Enantiomers are optically active stereoisomers so in order
to accomplish products with high enantiomeric excess, asymmetric synthesis must
be designed judiciously. Mimicking nature’s selective aptitude of biosynthesis is
always considered a crucial challenge for synthetic chemists. The main target of
drug designing is to attain skill in this specialized section. Racemization during asymmetric synthesis occasionally disappoints synthetic chemists by widely disrupting
biophysical, biochemical characteristics of the synthesized compound. Kinetic resolution, however, is able to separate two enantiomers. Among innumerable synthesis,
only a few are found to be associated with high enantiomeric excess yield. Contribution of enantioselective epoxide synthesis by Sharpless epoxidation is no less important in drug industry. Most striking feature of Sharpless epoxidation is materials used
for producing enantiospecific epoxide are inexpensive. Product spread consisting of
one predominating chiral epoxide is efficiently resolved. The current communication
is aimed to analyse Sharpless epoxidation from analytical angle of a chemist using
a model study of transition state structure using DIPT as chiral auxiliary and drives
to find the underlying basis responsible for channelizing only one enantiomer at the
suppression of other.
Keywords Diastereotopic TS · Kinetic resolution · Sharpless epoxidation
1 Introduction
The physiochemical activities are extremely specific. Almost all biochemical
responses are enzyme-controlled processes. Enzymes are chiral substances. The
degree of sensitivity is a function of chirality of the foreign moiety. In this circumstance, onus is on the synthetic chemists to synthesize enantiomerically pure
N. Paul (B)
Department of Chemistry, A.P.C Roy Govt. College, Siliguri, India
e-mail: paulnabanita367@gmail.com
© Springer Nature Singapore Pte Ltd. 2021
D. Ramkrishna et al. (eds.), Advances in Bioprocess Engineering and Technology,
Lecture Notes in Bioengineering,
https://doi.org/10.1007/978-981-15-7409-2_44
439