2020
DOI: 10.1021/acs.jchemed.9b00872
|View full text |Cite
|
Sign up to set email alerts
|

Asymmetric Synthesis and Absolute Configuration Determination of an Enantioenriched Alcohol: A Discovery-Based Undergraduate Laboratory Experiment

Abstract: An undergraduate organic chemistry experiment has been developed that features asymmetric synthesis of an enantioenriched secondary alcohol, followed by determination of its absolute configuration using the competing enantioselective conversion (CEC) method. Students are given a ketone and an unknown enantiomer of CBS (Corey–Bakshi–Shibata) catalyst. This reaction forms an enantioenriched secondary alcohol of unknown absolute configuration. Students then determine the absolute configuration via the CEC method.… Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
2
1
1

Citation Types

0
5
0

Year Published

2020
2020
2024
2024

Publication Types

Select...
4
1

Relationship

0
5

Authors

Journals

citations
Cited by 5 publications
(5 citation statements)
references
References 55 publications
0
5
0
Order By: Relevance
“…Acetophenone reduction using CBS in the presence of BMS is also part of King's synthesis and kinetic resolution laboratory experiment. 12 Although acetophenone reduction by sodium borohydride (Scheme 2) has been a part of our laboratory curriculum at Bridgewater College for over two decades, it was modified two years ago to include an additional week of asymmetric reduction and GC analysis. In the first year, it was part of a two-week laboratory experiment involving symmetric reduction using sodium borohydride.…”
Section: ■ Reduction Of Acetophenonementioning
confidence: 99%
See 2 more Smart Citations
“…Acetophenone reduction using CBS in the presence of BMS is also part of King's synthesis and kinetic resolution laboratory experiment. 12 Although acetophenone reduction by sodium borohydride (Scheme 2) has been a part of our laboratory curriculum at Bridgewater College for over two decades, it was modified two years ago to include an additional week of asymmetric reduction and GC analysis. In the first year, it was part of a two-week laboratory experiment involving symmetric reduction using sodium borohydride.…”
Section: ■ Reduction Of Acetophenonementioning
confidence: 99%
“…Recently, King and co-workers reported an experiment where an enantioenriched alcohol was synthesized in the first week and then reacted with an enantiomer of homobenzotetramisole. 12 The reaction rate, determined via TLC analysis, was then used to predict the dominant enantiomer of the alcohol. While this is a promising Both the chiral derivative analysis and kinetic resolution experiments could be completed in a single 3−4 h lab session with the addition of an appropriate chiral GC method.…”
Section: ■ Introductionmentioning
confidence: 99%
See 1 more Smart Citation
“…Methods for determining the absolute configuration of chiral molecules that have either been reported or are in use in most undergraduate curricula rely either on acid-base extraction followed by NMR or polarimetry 2,18,19 or on the determination of diastereomeric ratios of chiral derivatives using NMR, TLC, GC or HPLC analysis. [20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35] Herein described is how the addition and utility of gas chromatography (GC) data to two undergraduate organic chemistry experiments enables a better student experience of (1) the fact that the two sources of carvone lead to different isomers and (2) how the asymmetric reduction of acetophenone with a CBS catalyst produces an excess of one enantiomer compared to the non-catalyzed reaction which produces a racemic mixture of alcohol. The carvone experiment was completed in a single four-hour lab period, whereas the reduction experiment was conducted over two lab periods.…”
Section: Scheme 2: Mechanism For the Cbs-catalyzed Asymmetric Reducti...mentioning
confidence: 99%
“…2 The (R)-enantiomer is inactive but is gradually converted to the (S)-enantiomer. 3 Another example is citalopram, an antidepressant, a racemic mixture. However, its (R)-enantiomer, termed escitalopram, has been shown to have superior efficacy than citalopram.…”
mentioning
confidence: 99%