E- and chemoselective thia-Michael addition to benzyl allenoate

Rifhat Bibi; Amna Murtaza; Khalid Mohammed Khan; Zia ur Rehman; Aamer Saeed; Muhammad Nawaz Tahir; Abbas Hassan

doi:10.1080/10426507.2020.1799365

E- and chemoselective thia-Michael addition to benzyl allenoate

Rifhat Bibi
, Amna Murtaza
, Khalid Mohammed Khan
, Zia ur Rehman
, Aamer Saeed
, Muhammad Nawaz Tahir
, Abbas Hassan

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

5 Citations (Scopus)

Abstract

Different thiols were successfully reacted with benzyl allenoate resulting in E-selective thia-Michael addition product with α,β-unsaturation as confirmed by single crystal x-ray crystallographic analysis. The thia-Michael addition is chemoselective and free amine and alcohol groups were well tolerated. Catalytic triethylamine was required for high conversion. Fair to excellent yields were obtained for a variety of aliphatic, aryl and heteroaryl thiols.

Original language	English
Pages (from-to)	969-975
Number of pages	7
Journal	Phosphorus, Sulfur and Silicon and the Related Elements
Volume	195
Issue number	12
DOIs	https://doi.org/10.1080/10426507.2020.1799365
Publication status	Published - Jul 28 2020
Externally published	Yes

Keywords

chemoselective
E-selective
Thia-Michael addition
α-β-unsaturation
β-substituted thioenoates

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Inorganic Chemistry

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10.1080/10426507.2020.1799365

Cite this

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title = " E- and chemoselective thia-Michael addition to benzyl allenoate",

abstract = "Different thiols were successfully reacted with benzyl allenoate resulting in E-selective thia-Michael addition product with α,β-unsaturation as confirmed by single crystal x-ray crystallographic analysis. The thia-Michael addition is chemoselective and free amine and alcohol groups were well tolerated. Catalytic triethylamine was required for high conversion. Fair to excellent yields were obtained for a variety of aliphatic, aryl and heteroaryl thiols.",

keywords = "chemoselective, E-selective, Thia-Michael addition, α-β-unsaturation, β-substituted thioenoates",

author = "Rifhat Bibi and Amna Murtaza and Khan, \{Khalid Mohammed\} and Rehman, \{Zia ur\} and Aamer Saeed and Tahir, \{Muhammad Nawaz\} and Abbas Hassan",

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year = "2020",

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doi = "10.1080/10426507.2020.1799365",

language = "English",

volume = "195",

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journal = "Phosphorus, Sulfur and Silicon and the Related Elements",

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TY - JOUR

T1 - E- and chemoselective thia-Michael addition to benzyl allenoate

AU - Bibi, Rifhat

AU - Murtaza, Amna

AU - Khan, Khalid Mohammed

AU - Rehman, Zia ur

AU - Saeed, Aamer

AU - Tahir, Muhammad Nawaz

AU - Hassan, Abbas

PY - 2020/7/28

Y1 - 2020/7/28

N2 - Different thiols were successfully reacted with benzyl allenoate resulting in E-selective thia-Michael addition product with α,β-unsaturation as confirmed by single crystal x-ray crystallographic analysis. The thia-Michael addition is chemoselective and free amine and alcohol groups were well tolerated. Catalytic triethylamine was required for high conversion. Fair to excellent yields were obtained for a variety of aliphatic, aryl and heteroaryl thiols.

AB - Different thiols were successfully reacted with benzyl allenoate resulting in E-selective thia-Michael addition product with α,β-unsaturation as confirmed by single crystal x-ray crystallographic analysis. The thia-Michael addition is chemoselective and free amine and alcohol groups were well tolerated. Catalytic triethylamine was required for high conversion. Fair to excellent yields were obtained for a variety of aliphatic, aryl and heteroaryl thiols.

KW - chemoselective

KW - E-selective

KW - Thia-Michael addition

KW - α-β-unsaturation

KW - β-substituted thioenoates

UR - https://www.scopus.com/pages/publications/85088857890

UR - https://www.scopus.com/pages/publications/85088857890#tab=citedBy

U2 - 10.1080/10426507.2020.1799365

DO - 10.1080/10426507.2020.1799365

M3 - Article

AN - SCOPUS:85088857890

SN - 1042-6507

VL - 195

SP - 969

EP - 975

JO - Phosphorus, Sulfur and Silicon and the Related Elements

JF - Phosphorus, Sulfur and Silicon and the Related Elements

IS - 12

ER -

E- and chemoselective thia-Michael addition to benzyl allenoate

Abstract

Keywords

ASJC Scopus subject areas

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