Asymmetric cyclopropanations and cycloadditions of dioxocarbenes

Paul Müller, Yves Allenbach, Sabrina Chappellet, Ashraf Ghanem

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

Methods for enantioselective transfer of carbenes starting from precursors carrying two carbonyl groups have been elaborated. A one-pot procedure for olefin cyclopropanation with CH-acidic precursors via intermediate phenyliodonium ylides has been developed. The structure of the [Rh-2{(S)-nttl}4] catalyst was optimized to produce up to 98% ee in olefin cyclopropanations with dimethyl malonate or Meldrum's acid. Highly selective Rh(II)-catalyzed olefin cyclopropanations could be observed upon replacement of methyl diazoacetoacetate by methyl (silyloxyvinyl)diazoacetate. Enantioselective dipolar cycloadditions of diazopyruvate to polar olefins have been realized with Ru(II)-pybox catalysts
Original languageEnglish
Pages (from-to)1689-1696
Number of pages8
JournalSynthesis
Volume37
Issue number34
DOIs
Publication statusPublished - 2006
Externally publishedYes

Fingerprint

Cycloaddition
Alkenes
Olefins
Catalysts
Acids

Cite this

Müller, Paul ; Allenbach, Yves ; Chappellet, Sabrina ; Ghanem, Ashraf. / Asymmetric cyclopropanations and cycloadditions of dioxocarbenes. In: Synthesis. 2006 ; Vol. 37, No. 34. pp. 1689-1696.
@article{129d1064fc8d43a5937fe637d14e320b,
title = "Asymmetric cyclopropanations and cycloadditions of dioxocarbenes",
abstract = "Methods for enantioselective transfer of carbenes starting from precursors carrying two carbonyl groups have been elaborated. A one-pot procedure for olefin cyclopropanation with CH-acidic precursors via intermediate phenyliodonium ylides has been developed. The structure of the [Rh-2{(S)-nttl}4] catalyst was optimized to produce up to 98{\%} ee in olefin cyclopropanations with dimethyl malonate or Meldrum's acid. Highly selective Rh(II)-catalyzed olefin cyclopropanations could be observed upon replacement of methyl diazoacetoacetate by methyl (silyloxyvinyl)diazoacetate. Enantioselective dipolar cycloadditions of diazopyruvate to polar olefins have been realized with Ru(II)-pybox catalysts",
author = "Paul M{\"u}ller and Yves Allenbach and Sabrina Chappellet and Ashraf Ghanem",
year = "2006",
doi = "10.1002/chin.200634247",
language = "English",
volume = "37",
pages = "1689--1696",
journal = "Synthesis",
issn = "0039-7881",
publisher = "Georg Thieme Verlag",
number = "34",

}

Müller, P, Allenbach, Y, Chappellet, S & Ghanem, A 2006, 'Asymmetric cyclopropanations and cycloadditions of dioxocarbenes', Synthesis, vol. 37, no. 34, pp. 1689-1696. https://doi.org/10.1002/chin.200634247

Asymmetric cyclopropanations and cycloadditions of dioxocarbenes. / Müller, Paul; Allenbach, Yves; Chappellet, Sabrina; Ghanem, Ashraf.

In: Synthesis, Vol. 37, No. 34, 2006, p. 1689-1696.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Asymmetric cyclopropanations and cycloadditions of dioxocarbenes

AU - Müller, Paul

AU - Allenbach, Yves

AU - Chappellet, Sabrina

AU - Ghanem, Ashraf

PY - 2006

Y1 - 2006

N2 - Methods for enantioselective transfer of carbenes starting from precursors carrying two carbonyl groups have been elaborated. A one-pot procedure for olefin cyclopropanation with CH-acidic precursors via intermediate phenyliodonium ylides has been developed. The structure of the [Rh-2{(S)-nttl}4] catalyst was optimized to produce up to 98% ee in olefin cyclopropanations with dimethyl malonate or Meldrum's acid. Highly selective Rh(II)-catalyzed olefin cyclopropanations could be observed upon replacement of methyl diazoacetoacetate by methyl (silyloxyvinyl)diazoacetate. Enantioselective dipolar cycloadditions of diazopyruvate to polar olefins have been realized with Ru(II)-pybox catalysts

AB - Methods for enantioselective transfer of carbenes starting from precursors carrying two carbonyl groups have been elaborated. A one-pot procedure for olefin cyclopropanation with CH-acidic precursors via intermediate phenyliodonium ylides has been developed. The structure of the [Rh-2{(S)-nttl}4] catalyst was optimized to produce up to 98% ee in olefin cyclopropanations with dimethyl malonate or Meldrum's acid. Highly selective Rh(II)-catalyzed olefin cyclopropanations could be observed upon replacement of methyl diazoacetoacetate by methyl (silyloxyvinyl)diazoacetate. Enantioselective dipolar cycloadditions of diazopyruvate to polar olefins have been realized with Ru(II)-pybox catalysts

U2 - 10.1002/chin.200634247

DO - 10.1002/chin.200634247

M3 - Article

VL - 37

SP - 1689

EP - 1696

JO - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 34

ER -