Asymmetric cyclopropanations and cycloadditions of dioxocarbenes

Paul Müller; Yves Allenbach; Sabrina Chappellet; Ashraf Ghanem

doi:10.1002/chin.200634247

Asymmetric cyclopropanations and cycloadditions of dioxocarbenes

Paul Müller, Yves Allenbach, Sabrina Chappellet, Ashraf Ghanem

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

43 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 language	English
Pages (from-to)	1689-1696
Number of pages	8
Journal	Synthesis
Volume	37
Issue number	34
DOIs	https://doi.org/10.1002/chin.200634247
Publication status	Published - 2006
Externally published	Yes

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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",

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publisher = "Georg Thieme Verlag",

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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

SN - 0039-7881

VL - 37

SP - 1689

EP - 1696

JO - Synthesis

JF - Synthesis

IS - 34

ER -

Asymmetric cyclopropanations and cycloadditions of dioxocarbenes

Abstract

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