Synthesis of α-methylene-δ-oxo-γ-amino esters: Via Rh(II)-catalyzed coupling of 1-sulfonyl-1,2,3-triazoles with Morita-Baylis-Hillman adducts

Hyun Ji Jeon; Mi Soo Kwak; Da Jung Jung; Jean Bouffard; Sang Gi Lee

doi:10.1039/c6ob02086k

Synthesis of α-methylene-δ-oxo-γ-amino esters: Via Rh(II)-catalyzed coupling of 1-sulfonyl-1,2,3-triazoles with Morita-Baylis-Hillman adducts

Hyun Ji Jeon, Mi Soo Kwak, Da Jung Jung, Jean Bouffard, Sang Gi Lee

Department of Chemistry & Nanoscience

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

15 Scopus citations

Abstract

A rhodium(ii)-catalyzed coupling of 1-sulfonyl-1,2,3-triazoles, prepared from 1-alkynes and sulfonyl azides, with Morita-Baylis-Hillman (MBH) adducts afforded highly functionalized α-methylene-δ-oxo-γ-amino esters in excellent yields with broad functional group tolerance. This transformation can also be successfully accomplished as a multicomponent all-in-one-pot reaction of 1-alkynes, sulfonyl azides and MBH adducts in the presence of Cu(i) and Rh(ii) catalysts.

Original language	English
Pages (from-to)	11238-11243
Number of pages	6
Journal	Organic and Biomolecular Chemistry
Volume	14
Issue number	47
DOIs	https://doi.org/10.1039/c6ob02086k
State	Published - 2016

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© 2016 The Royal Society of Chemistry.

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title = "Synthesis of α-methylene-δ-oxo-γ-amino esters: Via Rh(II)-catalyzed coupling of 1-sulfonyl-1,2,3-triazoles with Morita-Baylis-Hillman adducts",

abstract = "A rhodium(ii)-catalyzed coupling of 1-sulfonyl-1,2,3-triazoles, prepared from 1-alkynes and sulfonyl azides, with Morita-Baylis-Hillman (MBH) adducts afforded highly functionalized α-methylene-δ-oxo-γ-amino esters in excellent yields with broad functional group tolerance. This transformation can also be successfully accomplished as a multicomponent all-in-one-pot reaction of 1-alkynes, sulfonyl azides and MBH adducts in the presence of Cu(i) and Rh(ii) catalysts.",

author = "Jeon, \{Hyun Ji\} and Kwak, \{Mi Soo\} and Jung, \{Da Jung\} and Jean Bouffard and Lee, \{Sang Gi\}",

note = "Publisher Copyright: {\textcopyright} 2016 The Royal Society of Chemistry.",

year = "2016",

doi = "10.1039/c6ob02086k",

language = "English",

volume = "14",

pages = "11238--11243",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

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TY - JOUR

T1 - Synthesis of α-methylene-δ-oxo-γ-amino esters

T2 - Via Rh(II)-catalyzed coupling of 1-sulfonyl-1,2,3-triazoles with Morita-Baylis-Hillman adducts

AU - Jeon, Hyun Ji

AU - Kwak, Mi Soo

AU - Jung, Da Jung

AU - Bouffard, Jean

AU - Lee, Sang Gi

PY - 2016

Y1 - 2016

N2 - A rhodium(ii)-catalyzed coupling of 1-sulfonyl-1,2,3-triazoles, prepared from 1-alkynes and sulfonyl azides, with Morita-Baylis-Hillman (MBH) adducts afforded highly functionalized α-methylene-δ-oxo-γ-amino esters in excellent yields with broad functional group tolerance. This transformation can also be successfully accomplished as a multicomponent all-in-one-pot reaction of 1-alkynes, sulfonyl azides and MBH adducts in the presence of Cu(i) and Rh(ii) catalysts.

AB - A rhodium(ii)-catalyzed coupling of 1-sulfonyl-1,2,3-triazoles, prepared from 1-alkynes and sulfonyl azides, with Morita-Baylis-Hillman (MBH) adducts afforded highly functionalized α-methylene-δ-oxo-γ-amino esters in excellent yields with broad functional group tolerance. This transformation can also be successfully accomplished as a multicomponent all-in-one-pot reaction of 1-alkynes, sulfonyl azides and MBH adducts in the presence of Cu(i) and Rh(ii) catalysts.

UR - https://www.scopus.com/pages/publications/84999693753

U2 - 10.1039/c6ob02086k

DO - 10.1039/c6ob02086k

M3 - Article

AN - SCOPUS:84999693753

SN - 1477-0520

VL - 14

SP - 11238

EP - 11243

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 47

ER -

Synthesis of α-methylene-δ-oxo-γ-amino esters: Via Rh(II)-catalyzed coupling of 1-sulfonyl-1,2,3-triazoles with Morita-Baylis-Hillman adducts

Abstract

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