Asymmetric Carbon−Carbon Bond Formation γ to a Carbonyl Group: Phosphine-Catalyzed Addition of Nitromethane to Allenes

Smith, Sean W. and Fu, Gregory C. (2009) Asymmetric Carbon−Carbon Bond Formation γ to a Carbonyl Group: Phosphine-Catalyzed Addition of Nitromethane to Allenes. Journal of the American Chemical Society, 131 (40). pp. 14231-14233. ISSN 0002-7863. PMCID PMC2758928. doi:10.1021/ja9061823. https://resolver.caltech.edu/CaltechAUTHORS:20200428-095147086

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Abstract

A chiral phosphine catalyzes the addition of a carbon nucleophile to the γ position of an electron-poor allene (amide-, ester-, or phosphonate-substituted), in preference to isomerization to a 1,3-diene, in good ee and yield. This strategy provides an attractive method for the catalytic asymmetric γ functionalization of carbonyl (and related) compounds.

Item Type:

Article

Related URLs:

URL	URL Type	Description
https://doi.org/10.1021/ja9061823	DOI	Article
http://www.ncbi.nlm.nih.gov/pmc/articles/pmc2758928/	PubMed Central	Article

ORCID:

Author	ORCID
Fu, Gregory C.	0000-0002-0927-680X

Additional Information:

© 2009 American Chemical Society. Received August 4, 2009. Support has been provided by the National Institutes of Health (National Institute of General Medical Sciences, Grant R01-GM57034), Merck Research Laboratories, and Novartis. We thank Dr. Nicolas Marion for assistance, Evonik Degussa for providing samples of phosphepines 1−4, and Prof. Qi-Lin Zhou for providing a precursor to phosphine 5. Funding for the MIT Department of Chemistry Instrumentation Facility has been furnished in part by NIH IS10RR13886 and NSF DBI-9729592.

Funders:

Funding Agency	Grant Number
NIH	R01-GM57034
Merck Research Laboratories	UNSPECIFIED
Novartis	UNSPECIFIED
NIH	IS10RR13886
NSF	DBI-9729592

Subject Keywords:

Functionalization; Hydrocarbons; Allenes; Substitution reactions; Catalysts

Issue or Number:

PubMed Central ID:

PMC2758928

DOI:

10.1021/ja9061823

Record Number:

CaltechAUTHORS:20200428-095147086

Persistent URL:

https://resolver.caltech.edu/CaltechAUTHORS:20200428-095147086

Official Citation:

Asymmetric Carbon−Carbon Bond Formation γ to a Carbonyl Group: Phosphine-Catalyzed Addition of Nitromethane to Allenes Sean W. Smith and Gregory C. Fu Journal of the American Chemical Society 2009 131 (40), 14231-14233 DOI: 10.1021/ja9061823

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No commercial reproduction, distribution, display or performance rights in this work are provided.

ID Code:

102867

Collection:

CaltechAUTHORS

Deposited By:

George Porter

Deposited On:

28 Apr 2020 19:11

Last Modified:

16 Nov 2021 18:16

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