Diastereoselectivity-switchable and highly enantioselective 1,3-dipolar cycloaddition of nitrones to alkylidene malonates

Zheng Zheng Huang; Yan Biao Kang; Jian Zhou; Meng Chun Ye; Yong Tang

doi:10.1021/ol049460d

Diastereoselectivity-switchable and highly enantioselective 1,3-dipolar cycloaddition of nitrones to alkylidene malonates

Zheng Zheng Huang
, Yan Biao Kang
, Jian Zhou
, Meng Chun Ye
, Yong Tang^*

^*Corresponding author for this work

CAS - Shanghai Institute of Organic Chemistry

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

90 Scopus citations

Abstract

Trisoxazoline 1/Co(ClO₄)₂·6H₂O catalyzed the 1,3-cycloaddition between nitrones 3 with alkylidene malonates 2 at 0°C to give the isoxazolidines with both high enantioselectivity and high exo selectivity. However, when the temperature was lowered from 0 to -40°C, the same cycloaddition afforded endo isomers as the major products with good to high enantioselectivity. A mechanism is provided.

Original language	English
Pages (from-to)	1677-1679
Number of pages	3
Journal	Organic Letters
Volume	6
Issue number	10
DOIs	https://doi.org/10.1021/ol049460d
State	Published - 13 May 2004
Externally published	Yes

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title = "Diastereoselectivity-switchable and highly enantioselective 1,3-dipolar cycloaddition of nitrones to alkylidene malonates",

abstract = "Trisoxazoline 1/Co(ClO4)2·6H2O catalyzed the 1,3-cycloaddition between nitrones 3 with alkylidene malonates 2 at 0°C to give the isoxazolidines with both high enantioselectivity and high exo selectivity. However, when the temperature was lowered from 0 to -40°C, the same cycloaddition afforded endo isomers as the major products with good to high enantioselectivity. A mechanism is provided.",

author = "Huang, \{Zheng Zheng\} and Kang, \{Yan Biao\} and Jian Zhou and Ye, \{Meng Chun\} and Yong Tang",

year = "2004",

month = may,

day = "13",

doi = "10.1021/ol049460d",

language = "英语",

volume = "6",

pages = "1677--1679",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "10",

}

TY - JOUR

T1 - Diastereoselectivity-switchable and highly enantioselective 1,3-dipolar cycloaddition of nitrones to alkylidene malonates

AU - Huang, Zheng Zheng

AU - Kang, Yan Biao

AU - Zhou, Jian

AU - Ye, Meng Chun

AU - Tang, Yong

PY - 2004/5/13

Y1 - 2004/5/13

N2 - Trisoxazoline 1/Co(ClO4)2·6H2O catalyzed the 1,3-cycloaddition between nitrones 3 with alkylidene malonates 2 at 0°C to give the isoxazolidines with both high enantioselectivity and high exo selectivity. However, when the temperature was lowered from 0 to -40°C, the same cycloaddition afforded endo isomers as the major products with good to high enantioselectivity. A mechanism is provided.

AB - Trisoxazoline 1/Co(ClO4)2·6H2O catalyzed the 1,3-cycloaddition between nitrones 3 with alkylidene malonates 2 at 0°C to give the isoxazolidines with both high enantioselectivity and high exo selectivity. However, when the temperature was lowered from 0 to -40°C, the same cycloaddition afforded endo isomers as the major products with good to high enantioselectivity. A mechanism is provided.

UR - https://www.scopus.com/pages/publications/2542592576

U2 - 10.1021/ol049460d

DO - 10.1021/ol049460d

M3 - 文章

AN - SCOPUS:2542592576

SN - 1523-7060

VL - 6

SP - 1677

EP - 1679

JO - Organic Letters

JF - Organic Letters

IS - 10

ER -

Diastereoselectivity-switchable and highly enantioselective 1,3-dipolar cycloaddition of nitrones to alkylidene malonates

Abstract

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