Stereoselective synthesis of β-amino-α-fluoro esters via diastereoselective fluorination of enantiopure β-amino enolates

Philip C. Andrews; Vijaya Bhaskar; Karen M. Bromfield; Aileen M. Dodd; Peter J. Duggan; Sandhya A.M. Duggan; Tom D. McCarthy

doi:10.1055/s-2004-817782

Stereoselective synthesis of β-amino-α-fluoro esters via diastereoselective fluorination of enantiopure β-amino enolates

Philip C. Andrews, Vijaya Bhaskar, Karen M. Bromfield, Aileen M. Dodd, Peter J. Duggan, Sandhya A.M. Duggan, Tom D. McCarthy

Research output: Contribution to journal › Article › peer-review

35 Citations (Scopus)

Abstract

β-Amino-α-fluoro esters have been prepared stereoselectively from t-butyl cinnamate and ethyl crotonate via tandem conjugate addition of lithium (S)-(-)-N-benzyl-N-α-methylbenzylamide, followed by fluorination with N-fluorobenzenesulfonimide. The absolute stereochemistry of the major diastereomers formed in each reaction was confirmed by X-ray crystallography. Complete deprotection to give (25,3S)-α-fluoro-β-phenylalanine followed by Fmoc protection was achieved.

Original language	English
Pages (from-to)	791-794
Number of pages	4
Journal	SYNLETT
Issue number	5
DOIs	https://doi.org/10.1055/s-2004-817782
Publication status	Published - Apr 2004
Externally published	Yes

Keywords

Conjugate additions
Diastereoselectivity
Fluorination
Lithium amides
β-amino acids

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title = "Stereoselective synthesis of β-amino-α-fluoro esters via diastereoselective fluorination of enantiopure β-amino enolates",

abstract = "β-Amino-α-fluoro esters have been prepared stereoselectively from t-butyl cinnamate and ethyl crotonate via tandem conjugate addition of lithium (S)-(-)-N-benzyl-N-α-methylbenzylamide, followed by fluorination with N-fluorobenzenesulfonimide. The absolute stereochemistry of the major diastereomers formed in each reaction was confirmed by X-ray crystallography. Complete deprotection to give (25,3S)-α-fluoro-β-phenylalanine followed by Fmoc protection was achieved.",

keywords = "Conjugate additions, Diastereoselectivity, Fluorination, Lithium amides, β-amino acids",

author = "Andrews, {Philip C.} and Vijaya Bhaskar and Bromfield, {Karen M.} and Dodd, {Aileen M.} and Duggan, {Peter J.} and Duggan, {Sandhya A.M.} and McCarthy, {Tom D.}",

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doi = "10.1055/s-2004-817782",

language = "English",

pages = "791--794",

journal = "SYNLETT",

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T1 - Stereoselective synthesis of β-amino-α-fluoro esters via diastereoselective fluorination of enantiopure β-amino enolates

AU - Andrews, Philip C.

AU - Bhaskar, Vijaya

AU - Bromfield, Karen M.

AU - Dodd, Aileen M.

AU - Duggan, Peter J.

AU - Duggan, Sandhya A.M.

AU - McCarthy, Tom D.

PY - 2004/4

Y1 - 2004/4

N2 - β-Amino-α-fluoro esters have been prepared stereoselectively from t-butyl cinnamate and ethyl crotonate via tandem conjugate addition of lithium (S)-(-)-N-benzyl-N-α-methylbenzylamide, followed by fluorination with N-fluorobenzenesulfonimide. The absolute stereochemistry of the major diastereomers formed in each reaction was confirmed by X-ray crystallography. Complete deprotection to give (25,3S)-α-fluoro-β-phenylalanine followed by Fmoc protection was achieved.

AB - β-Amino-α-fluoro esters have been prepared stereoselectively from t-butyl cinnamate and ethyl crotonate via tandem conjugate addition of lithium (S)-(-)-N-benzyl-N-α-methylbenzylamide, followed by fluorination with N-fluorobenzenesulfonimide. The absolute stereochemistry of the major diastereomers formed in each reaction was confirmed by X-ray crystallography. Complete deprotection to give (25,3S)-α-fluoro-β-phenylalanine followed by Fmoc protection was achieved.

KW - Conjugate additions

KW - Diastereoselectivity

KW - Fluorination

KW - Lithium amides

KW - β-amino acids

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DO - 10.1055/s-2004-817782

M3 - Article

AN - SCOPUS:1942457208

SN - 0936-5214

SP - 791

EP - 794

JO - SYNLETT

JF - SYNLETT

IS - 5

ER -

Stereoselective synthesis of β-amino-α-fluoro esters via diastereoselective fluorination of enantiopure β-amino enolates

Abstract

Keywords

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