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^*

^*此作品的通讯作者

CAS - Shanghai Institute of Organic Chemistry

科研成果: 期刊稿件 › 文章 › 同行评审

90 引用（Scopus）

摘要

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.

源语言	英语
页（从-至）	1677-1679
页数	3
期刊	Organic Letters
卷	6
期	10
DOI	https://doi.org/10.1021/ol049460d
出版状态	已出版 - 13 5月 2004
已对外发布	是

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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",

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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

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