Highly diastereoselective synthesis of optically pure trifluoromethyl- substituted imidazolidine, oxazolidine and thiazolidine

Honghai Zhang; Qilong Shen; Long Lu

doi:10.1016/j.tetlet.2010.11.061

Highly diastereoselective synthesis of optically pure trifluoromethyl- substituted imidazolidine, oxazolidine and thiazolidine

Honghai Zhang
, Qilong Shen
, Long Lu

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

15 Scopus citations

Abstract

Optically pure trifluoromethylated imidazolidine, oxazolidine, and thiazolidine derivatives were synthesized through double Michael addition of chiral amino amides, amino acids, or amino alcohols to an easily available trifluoromethyl building block methyl (Z)-2-bromo-4,4,4-trifluoro-2-butenoate. These reactions occurred highly diastereo-selectively (up to 99:1) in good yields (65-96%) under mild conditions.

Original language	English
Pages (from-to)	349-351
Number of pages	3
Journal	Tetrahedron Letters
Volume	52
Issue number	2
DOIs	https://doi.org/10.1016/j.tetlet.2010.11.061
State	Published - Jan 12 2011
Externally published	Yes

Funding

The authors gratefully acknowledge the financial support from the National Natural Science Foundation of China (Grant Number 29825104 and 29632003 ), the project of Application of Nuclear Techniques in Agriculture ( 200803034 ), the Key Program of National Natural Science Foundation of China ( 20632070 ), the National Basic ResearchProgram of China ( 2010CB126103 ), and the SIOC startup fund (QS) for financial support.

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10.1016/j.tetlet.2010.11.061

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title = "Highly diastereoselective synthesis of optically pure trifluoromethyl- substituted imidazolidine, oxazolidine and thiazolidine",

abstract = "Optically pure trifluoromethylated imidazolidine, oxazolidine, and thiazolidine derivatives were synthesized through double Michael addition of chiral amino amides, amino acids, or amino alcohols to an easily available trifluoromethyl building block methyl (Z)-2-bromo-4,4,4-trifluoro-2-butenoate. These reactions occurred highly diastereo-selectively (up to 99:1) in good yields (65-96\%) under mild conditions.",

author = "Honghai Zhang and Qilong Shen and Long Lu",

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doi = "10.1016/j.tetlet.2010.11.061",

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journal = "Tetrahedron Letters",

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T1 - Highly diastereoselective synthesis of optically pure trifluoromethyl- substituted imidazolidine, oxazolidine and thiazolidine

AU - Zhang, Honghai

AU - Shen, Qilong

AU - Lu, Long

PY - 2011/1/12

Y1 - 2011/1/12

N2 - Optically pure trifluoromethylated imidazolidine, oxazolidine, and thiazolidine derivatives were synthesized through double Michael addition of chiral amino amides, amino acids, or amino alcohols to an easily available trifluoromethyl building block methyl (Z)-2-bromo-4,4,4-trifluoro-2-butenoate. These reactions occurred highly diastereo-selectively (up to 99:1) in good yields (65-96%) under mild conditions.

AB - Optically pure trifluoromethylated imidazolidine, oxazolidine, and thiazolidine derivatives were synthesized through double Michael addition of chiral amino amides, amino acids, or amino alcohols to an easily available trifluoromethyl building block methyl (Z)-2-bromo-4,4,4-trifluoro-2-butenoate. These reactions occurred highly diastereo-selectively (up to 99:1) in good yields (65-96%) under mild conditions.

UR - https://www.scopus.com/pages/publications/78650028793

U2 - 10.1016/j.tetlet.2010.11.061

DO - 10.1016/j.tetlet.2010.11.061

M3 - Article

AN - SCOPUS:78650028793

SN - 0040-4039

VL - 52

SP - 349

EP - 351

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 2

ER -

Highly diastereoselective synthesis of optically pure trifluoromethyl- substituted imidazolidine, oxazolidine and thiazolidine

Abstract

Funding

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