Highly enantioselective catalytic 1,3-dipolar cycloadditions of α-alkyl diazoacetates: Efficient synthesis of functionalized 2-pyrazolines

Sung Il Lee; Ka Eun Kim; Geum Sook Hwang; Do Hyun Ryu

doi:10.1039/c4ob02372b

Highly enantioselective catalytic 1,3-dipolar cycloadditions of α-alkyl diazoacetates: Efficient synthesis of functionalized 2-pyrazolines

Sung Il Lee, Ka Eun Kim, Geum Sook Hwang, Do Hyun Ryu

Department of Chemistry

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25 Scopus citations

Abstract

Highly enantioselective 1,3-dipolar cycloaddition reactions of α-substituted diazoacetates are accomplished by catalysis of the chiral oxazaborolidinium ion. Functionalized 2-pyrazolines are synthesized in high to excellent enantiomeric ratios (up to >99:1). The synthetic utility of 2-pyrazoline was expanded via preparation of 2,4-diamino ester compounds bearing a chiral quaternary carbon center.

Original language	English
Pages (from-to)	2745-2749
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	13
Issue number	9
DOIs	https://doi.org/10.1039/c4ob02372b
State	Published - 7 Mar 2015

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title = "Highly enantioselective catalytic 1,3-dipolar cycloadditions of α-alkyl diazoacetates: Efficient synthesis of functionalized 2-pyrazolines",

abstract = "Highly enantioselective 1,3-dipolar cycloaddition reactions of α-substituted diazoacetates are accomplished by catalysis of the chiral oxazaborolidinium ion. Functionalized 2-pyrazolines are synthesized in high to excellent enantiomeric ratios (up to >99:1). The synthetic utility of 2-pyrazoline was expanded via preparation of 2,4-diamino ester compounds bearing a chiral quaternary carbon center.",

author = "Lee, \{Sung Il\} and Kim, \{Ka Eun\} and Hwang, \{Geum Sook\} and Ryu, \{Do Hyun\}",

note = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry.",

year = "2015",

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doi = "10.1039/c4ob02372b",

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T1 - Highly enantioselective catalytic 1,3-dipolar cycloadditions of α-alkyl diazoacetates

T2 - Efficient synthesis of functionalized 2-pyrazolines

AU - Lee, Sung Il

AU - Kim, Ka Eun

AU - Hwang, Geum Sook

AU - Ryu, Do Hyun

N1 - Publisher Copyright: © The Royal Society of Chemistry.

PY - 2015/3/7

Y1 - 2015/3/7

N2 - Highly enantioselective 1,3-dipolar cycloaddition reactions of α-substituted diazoacetates are accomplished by catalysis of the chiral oxazaborolidinium ion. Functionalized 2-pyrazolines are synthesized in high to excellent enantiomeric ratios (up to >99:1). The synthetic utility of 2-pyrazoline was expanded via preparation of 2,4-diamino ester compounds bearing a chiral quaternary carbon center.

AB - Highly enantioselective 1,3-dipolar cycloaddition reactions of α-substituted diazoacetates are accomplished by catalysis of the chiral oxazaborolidinium ion. Functionalized 2-pyrazolines are synthesized in high to excellent enantiomeric ratios (up to >99:1). The synthetic utility of 2-pyrazoline was expanded via preparation of 2,4-diamino ester compounds bearing a chiral quaternary carbon center.

UR - https://www.scopus.com/pages/publications/84923359410

U2 - 10.1039/c4ob02372b

DO - 10.1039/c4ob02372b

M3 - Article

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AN - SCOPUS:84923359410

SN - 1477-0520

VL - 13

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EP - 2749

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 9

ER -

Highly enantioselective catalytic 1,3-dipolar cycloadditions of α-alkyl diazoacetates: Efficient synthesis of functionalized 2-pyrazolines

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