Extensive studies on the AlEt3/THF-promoted diastereoseletive tandem rearrangement/reduction of α-hydroxy (amino) heterocyclopropane: An efficient approach to 2-quaternary 1,3-diheteroatom units

Xin Li; Bao Min Wang; Xue Zhi Zhao; Shuan Hu Gao; Yong Qiang Tu; De Run Li

doi:10.1002/cjoc.20040221024

Extensive studies on the AlEt₃/THF-promoted diastereoseletive tandem rearrangement/reduction of α-hydroxy (amino) heterocyclopropane: An efficient approach to 2-quaternary 1,3-diheteroatom units

Xin Li, Bao Min Wang, Xue Zhi Zhao, Shuan Hu Gao, Yong Qiang Tu, De Run Li

Lanzhou University

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

5 Scopus citations

Abstract

A facile and highly diastereoselective method for the construction of 2-quaternary 1,3-amino alcohols and 1,3-diols has been developed on the basis of the AlE₃/THF-promoted tandem rearrangement/reductive reaction of α-hydroxy (amino) aziridines (epoxides). The progressive achievement in this article included that both 2-epimers of the units could be constructed from the initially same substrate. Also a stereochemistry assignment we reported previously was corrected.

Original language	English
Pages (from-to)	1177-1182
Number of pages	6
Journal	Chinese Journal of Chemistry
Volume	22
Issue number	10
DOIs	https://doi.org/10.1002/cjoc.20040221024
State	Published - Oct 2004
Externally published	Yes

Keywords

Amino alcohol
Diastereoselectivity
Quaternary carbon
Tandem reaction
Triethyl aluminium

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10.1002/cjoc.20040221024

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title = "Extensive studies on the AlEt3/THF-promoted diastereoseletive tandem rearrangement/reduction of α-hydroxy (amino) heterocyclopropane: An efficient approach to 2-quaternary 1,3-diheteroatom units",

abstract = "A facile and highly diastereoselective method for the construction of 2-quaternary 1,3-amino alcohols and 1,3-diols has been developed on the basis of the AlE3/THF-promoted tandem rearrangement/reductive reaction of α-hydroxy (amino) aziridines (epoxides). The progressive achievement in this article included that both 2-epimers of the units could be constructed from the initially same substrate. Also a stereochemistry assignment we reported previously was corrected.",

keywords = "Amino alcohol, Diastereoselectivity, Quaternary carbon, Tandem reaction, Triethyl aluminium",

author = "Xin Li and Wang, \{Bao Min\} and Zhao, \{Xue Zhi\} and Gao, \{Shuan Hu\} and Tu, \{Yong Qiang\} and Li, \{De Run\}",

year = "2004",

month = oct,

doi = "10.1002/cjoc.20040221024",

language = "英语",

volume = "22",

pages = "1177--1182",

journal = "Chinese Journal of Chemistry",

issn = "1001-604X",

publisher = "John Wiley and Sons Inc",

number = "10",

}

Extensive studies on the AlEt₃/THF-promoted diastereoseletive tandem rearrangement/reduction of α-hydroxy (amino) heterocyclopropane: An efficient approach to 2-quaternary 1,3-diheteroatom units. / Li, Xin; Wang, Bao Min; Zhao, Xue Zhi et al.
In: Chinese Journal of Chemistry, Vol. 22, No. 10, 10.2004, p. 1177-1182.

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

TY - JOUR

T1 - Extensive studies on the AlEt3/THF-promoted diastereoseletive tandem rearrangement/reduction of α-hydroxy (amino) heterocyclopropane

T2 - An efficient approach to 2-quaternary 1,3-diheteroatom units

AU - Li, Xin

AU - Wang, Bao Min

AU - Zhao, Xue Zhi

AU - Gao, Shuan Hu

AU - Tu, Yong Qiang

AU - Li, De Run

PY - 2004/10

Y1 - 2004/10

N2 - A facile and highly diastereoselective method for the construction of 2-quaternary 1,3-amino alcohols and 1,3-diols has been developed on the basis of the AlE3/THF-promoted tandem rearrangement/reductive reaction of α-hydroxy (amino) aziridines (epoxides). The progressive achievement in this article included that both 2-epimers of the units could be constructed from the initially same substrate. Also a stereochemistry assignment we reported previously was corrected.

AB - A facile and highly diastereoselective method for the construction of 2-quaternary 1,3-amino alcohols and 1,3-diols has been developed on the basis of the AlE3/THF-promoted tandem rearrangement/reductive reaction of α-hydroxy (amino) aziridines (epoxides). The progressive achievement in this article included that both 2-epimers of the units could be constructed from the initially same substrate. Also a stereochemistry assignment we reported previously was corrected.

KW - Amino alcohol

KW - Diastereoselectivity

KW - Quaternary carbon

KW - Tandem reaction

KW - Triethyl aluminium

UR - https://www.scopus.com/pages/publications/9644265670

U2 - 10.1002/cjoc.20040221024

DO - 10.1002/cjoc.20040221024

M3 - 文章

AN - SCOPUS:9644265670

SN - 1001-604X

VL - 22

SP - 1177

EP - 1182

JO - Chinese Journal of Chemistry

JF - Chinese Journal of Chemistry

IS - 10

ER -

Extensive studies on the AlEt₃/THF-promoted diastereoseletive tandem rearrangement/reduction of α-hydroxy (amino) heterocyclopropane: An efficient approach to 2-quaternary 1,3-diheteroatom units

Abstract

Keywords

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