What question did this study set out to answer?

To establish an enantioselective synthetic pathway for producing R-(+)-α-lipoic acid from readily accessible starting materials.

January 1, 1990Journal of the Chemical Society Perkin Transactions 1

An enantioselective synthesis of R-(+)-α-lipoic acid

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To establish an enantioselective synthetic pathway for producing R-(+)-α-lipoic acid from readily accessible starting materials.
Executed a six-step organic synthesis originating from 6-bromohex-1-ene.
Employed Sharpless asymmetric epoxidation on an intermediate allyl alcohol to dictate the stereochemical outcome.
Successfully produced R-(+)-α-lipoic acid across a six-step sequence.
Achieved an optical rotation of [α]D +107° for the resulting product, verifying asymmetric induction.

Implication

Synthetic chemistry study demonstrates enantioselective synthesis of R-(+)-alpha-lipoic acid from 6-bromohex-1-ene, highlighting Sharpless epoxidation for stereocontrol.

Abstract

R-(+)-α-Lipoic acid (1), [α]D+107°, has been prepared in a six-step enantioselective synthesis from 6-bromohex-1-ene; the enantioselectivity is controlled by a Sharpless asymmetric epoxidation of the intermediate allyl alcohol (2).

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Cite This Study

Page et al. (1990) studied this question.

synapsesocial.com/papers/6a9cd56a7f3bc4118e598f00 https://doi.org/10.1039/p19900001615

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Implication

Synthetic chemistry study demonstrates enantioselective synthesis of R-(+)-alpha-lipoic acid from 6-bromohex-1-ene, highlighting Sharpless epoxidation for stereocontrol.

An enantioselective synthesis of R-(+)-α-lipoic acid

Key Points

Implication

Abstract

Discussion

Cite This Study

An enantioselective synthesis of R-(+)-α-lipoic acid

Key Points

Implication

Abstract

Discussion

Cite This Study

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