Synthesis of N-Boc-3-amino-1,2-epoxy-4-phenylbutane from (3S)-Hydroxy-γ-butyrolactone by Means of the Hofmann Rearrangement

The Fráter-Seebach alkylation is a highly efficient means to diastereoselectively introduce α-substituents to chiral β-hydroxy esters, however, the yields of reactions in which longer chain alkyl halides are used can be disappointing. To provide a more robust protocol for the alkylation of β-hydroxy esters, we prepared a variety of long-chain allylic iodides with the view that the greater reactivity of the allylic system would

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The Synthesis of Long‐Chain α‐Alkyl‐β‐Hydroxy Esters Using Allylic Halides in a Fráter–Seebach Alkylation

Khan

Chee

Stocker

et al. 2011

Eur J Org Chem

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Tailor-made amino acids in the design of small-molecule blockbuster drugs

Han

Konno

Sato

et al. 2021

European Journal of Medicinal Chemistry

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Industrial Syntheses of the Central Core Molecules of HIV Protease Inhibitors

Izawa

Onishi

2006

Chem. Rev.

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Synthesis of N-Boc-3-amino-1,2-epoxy-4-phenylbutane from (3S)-Hydroxy-γ-butyrolactone by Means of the Hofmann Rearrangement

Cited by 4 publications

References 7 publications

The Synthesis of Long‐Chain α‐Alkyl‐β‐Hydroxy Esters Using Allylic Halides in a Fráter–Seebach Alkylation

The Synthesis of Long‐Chain α‐Alkyl‐β‐Hydroxy Esters Using Allylic Halides in a Fráter–Seebach Alkylation

Tailor-made amino acids in the design of small-molecule blockbuster drugs

Industrial Syntheses of the Central Core Molecules of HIV Protease Inhibitors

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