The use of enantiomerically pure ketene dithioacetal bis(sulfoxides) in highly diastereoselective intramolecular nitrone cycloadditions. Application in the total synthesis of the beta-amino acid (-)-cispentacin and the first asymmetric synthesis of cis-(3R,4R)-4-amino-pyrrolidine-3-carboxylic acid

VK Aggarwal; S Roseblade; Rikki Alexander

doi:10.1039/b212719a

The use of enantiomerically pure ketene dithioacetal bis(sulfoxides) in highly diastereoselective intramolecular nitrone cycloadditions. Application in the total synthesis of the beta-amino acid (-)-cispentacin and the first asymmetric synthesis of cis-(3R,4R)-4-amino-pyrrolidine-3-carboxylic acid

VK Aggarwal^*
, S Roseblade
, Rikki Alexander

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

56 Citations (Scopus)

Abstract

Intramolecular 1,3-dipolar nitrone cycloaddition onto an enantiomerically pure ketene dithioacetal dioxide using a three-carbon tether gave the corresponding 5,5-disubstituted isoxazolidine as a single diastereomer in good yield. This reaction has been used as the key step in an asymmetric synthesis of the naturally occurring antibiotic, (-)-cispentacin. An asymmetric synthesis-of 4-amino-pyrrolidine-3-carboxylic acid has also been carried out using the intramolecular nitrone cycloaddition as the stereocontrolling step.

Original language	English
Pages (from-to)	684-691
Number of pages	8
Journal	Organic and Biomolecular Chemistry
Volume	1
Issue number	4
DOIs	https://doi.org/10.1039/b212719a
Publication status	Published - 21 Feb 2003

Research Groups and Themes

Organic & Biological

Keywords

DIELS-ALDER REACTIONS
PHYSICOCHEMICAL PROPERTIES
N-OXIDE
CISPENTACIN
FR109615
2-ALKYL-5-METHYLENE-1,3-DIOXOLAN-4-ONES
INTERMEDIATE
NITROALKENES
1,3-DIOXIDE
EQUIVALENTS

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Aggarwal, VK., Roseblade, S., & Alexander, R. (2003). The use of enantiomerically pure ketene dithioacetal bis(sulfoxides) in highly diastereoselective intramolecular nitrone cycloadditions. Application in the total synthesis of the beta-amino acid (-)-cispentacin and the first asymmetric synthesis of cis-(3R,4R)-4-amino-pyrrolidine-3-carboxylic acid. Organic and Biomolecular Chemistry, 1(4), 684-691. https://doi.org/10.1039/b212719a

Aggarwal, VK ; Roseblade, S ; Alexander, Rikki. / The use of enantiomerically pure ketene dithioacetal bis(sulfoxides) in highly diastereoselective intramolecular nitrone cycloadditions. Application in the total synthesis of the beta-amino acid (-)-cispentacin and the first asymmetric synthesis of cis-(3R,4R)-4-amino-pyrrolidine-3-carboxylic acid. In: Organic and Biomolecular Chemistry. 2003 ; Vol. 1, No. 4. pp. 684-691.

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title = "The use of enantiomerically pure ketene dithioacetal bis(sulfoxides) in highly diastereoselective intramolecular nitrone cycloadditions. Application in the total synthesis of the beta-amino acid (-)-cispentacin and the first asymmetric synthesis of cis-(3R,4R)-4-amino-pyrrolidine-3-carboxylic acid",

abstract = "Intramolecular 1,3-dipolar nitrone cycloaddition onto an enantiomerically pure ketene dithioacetal dioxide using a three-carbon tether gave the corresponding 5,5-disubstituted isoxazolidine as a single diastereomer in good yield. This reaction has been used as the key step in an asymmetric synthesis of the naturally occurring antibiotic, (-)-cispentacin. An asymmetric synthesis-of 4-amino-pyrrolidine-3-carboxylic acid has also been carried out using the intramolecular nitrone cycloaddition as the stereocontrolling step.",

keywords = "DIELS-ALDER REACTIONS, PHYSICOCHEMICAL PROPERTIES, N-OXIDE, CISPENTACIN, FR109615, 2-ALKYL-5-METHYLENE-1,3-DIOXOLAN-4-ONES, INTERMEDIATE, NITROALKENES, 1,3-DIOXIDE, EQUIVALENTS",

author = "VK Aggarwal and S Roseblade and Rikki Alexander",

year = "2003",

month = feb,

day = "21",

doi = "10.1039/b212719a",

language = "English",

volume = "1",

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journal = "Organic and Biomolecular Chemistry",

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Aggarwal, VK, Roseblade, S & Alexander, R 2003, 'The use of enantiomerically pure ketene dithioacetal bis(sulfoxides) in highly diastereoselective intramolecular nitrone cycloadditions. Application in the total synthesis of the beta-amino acid (-)-cispentacin and the first asymmetric synthesis of cis-(3R,4R)-4-amino-pyrrolidine-3-carboxylic acid', Organic and Biomolecular Chemistry, vol. 1, no. 4, pp. 684-691. https://doi.org/10.1039/b212719a

The use of enantiomerically pure ketene dithioacetal bis(sulfoxides) in highly diastereoselective intramolecular nitrone cycloadditions. Application in the total synthesis of the beta-amino acid (-)-cispentacin and the first asymmetric synthesis of cis-(3R,4R)-4-amino-pyrrolidine-3-carboxylic acid. / Aggarwal, VK; Roseblade, S; Alexander, Rikki.
In: Organic and Biomolecular Chemistry, Vol. 1, No. 4, 21.02.2003, p. 684-691.

Research output: Contribution to journal › Article (Academic Journal) › peer-review

TY - JOUR

T1 - The use of enantiomerically pure ketene dithioacetal bis(sulfoxides) in highly diastereoselective intramolecular nitrone cycloadditions. Application in the total synthesis of the beta-amino acid (-)-cispentacin and the first asymmetric synthesis of cis-(3R,4R)-4-amino-pyrrolidine-3-carboxylic acid

AU - Aggarwal, VK

AU - Roseblade, S

AU - Alexander, Rikki

PY - 2003/2/21

Y1 - 2003/2/21

N2 - Intramolecular 1,3-dipolar nitrone cycloaddition onto an enantiomerically pure ketene dithioacetal dioxide using a three-carbon tether gave the corresponding 5,5-disubstituted isoxazolidine as a single diastereomer in good yield. This reaction has been used as the key step in an asymmetric synthesis of the naturally occurring antibiotic, (-)-cispentacin. An asymmetric synthesis-of 4-amino-pyrrolidine-3-carboxylic acid has also been carried out using the intramolecular nitrone cycloaddition as the stereocontrolling step.

AB - Intramolecular 1,3-dipolar nitrone cycloaddition onto an enantiomerically pure ketene dithioacetal dioxide using a three-carbon tether gave the corresponding 5,5-disubstituted isoxazolidine as a single diastereomer in good yield. This reaction has been used as the key step in an asymmetric synthesis of the naturally occurring antibiotic, (-)-cispentacin. An asymmetric synthesis-of 4-amino-pyrrolidine-3-carboxylic acid has also been carried out using the intramolecular nitrone cycloaddition as the stereocontrolling step.

KW - DIELS-ALDER REACTIONS

KW - PHYSICOCHEMICAL PROPERTIES

KW - N-OXIDE

KW - CISPENTACIN

KW - FR109615

KW - 2-ALKYL-5-METHYLENE-1,3-DIOXOLAN-4-ONES

KW - INTERMEDIATE

KW - NITROALKENES

KW - 1,3-DIOXIDE

KW - EQUIVALENTS

U2 - 10.1039/b212719a

DO - 10.1039/b212719a

M3 - Article (Academic Journal)

SN - 1477-0520

VL - 1

SP - 684

EP - 691

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 4

ER -

Aggarwal VK, Roseblade S, Alexander R. The use of enantiomerically pure ketene dithioacetal bis(sulfoxides) in highly diastereoselective intramolecular nitrone cycloadditions. Application in the total synthesis of the beta-amino acid (-)-cispentacin and the first asymmetric synthesis of cis-(3R,4R)-4-amino-pyrrolidine-3-carboxylic acid. Organic and Biomolecular Chemistry. 2003 Feb 21;1(4):684-691. doi: 10.1039/b212719a