Phosphine-catalyzed asymmetric additions of malonate esters to γ-substituted allenoates and allenamides

Sinisi, Riccardo and Sun, Jianwei and Fu, Gregory C. (2010) Phosphine-catalyzed asymmetric additions of malonate esters to γ-substituted allenoates and allenamides. Proceedings of the National Academy of Sciences of the United States of America, 107 (48). pp. 20652-20654. ISSN 0027-8424. PMCID PMC2996437. doi:10.1073/pnas.1003597107. https://resolver.caltech.edu/CaltechAUTHORS:20200513-150749013

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Abstract

Because carbonyl groups are ubiquitous in organic chemistry, the ability to synthesize functionalized carbonyl compounds, particularly enantioselectively, is an important objective. We have developed a straightforward and versatile method for catalytic asymmetric carbon–carbon bond formation at the γ-position of carbonyl compounds, specifically, phosphine-catalyzed additions of malonate esters to γ-substituted allenoates and allenamides. Mechanistic studies have provided insight into the reaction pathway.

Item Type:

Article

Related URLs:

URL	URL Type	Description
https://doi.org/10.1073/pnas.1003597107	DOI	Article
https://www.pnas.org/content/suppl/2010/07/12/1003597107.DCSupplemental	Publisher	Supporting Information
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2996437	PubMed Central	Article

ORCID:

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

Additional Information:

© 2010 National Academy of Sciences. Edited by David W. C. MacMillan, Princeton University, Princeton, NJ, and accepted by the Editorial Board May 30, 2010 (received for review March 18, 2010). PNAS first published July 12, 2010. We thank Dr. Sean W. Smith for preliminary studies and Dr. Meiliana Tjandra and Shaun D. Fontaine for experimental assistance. Support has been provided by the National Institutes of Health (National Institute of General Medical Sciences, Grant R01-GM57034), the University of Bologna (Marco Polo fellowship for R.S.), Merck Research Laboratories, and Novartis. R.S. and J.S. contributed equally to this work. Author contributions: R.S., J.S., and G.C.F. designed research; R.S. and J.S. performed research; R.S., J.S., and G.C.F. analyzed data; and J.S. and G.C.F. wrote the paper. The authors declare no conflict of interest. This article is a PNAS Direct Submission. D.W.M. is a guest editor invited by the Editorial Board. This article contains supporting information online at www.pnas.org/lookup/suppl/doi:10.1073/pnas.1003597107/-/DCSupplemental.

Funders:

Funding Agency	Grant Number
NIH	R01-GM57034
University of Bologna	UNSPECIFIED
Merck Research Laboratories	UNSPECIFIED
Novartis	UNSPECIFIED

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PubMed Central ID:

PMC2996437

DOI:

10.1073/pnas.1003597107

Record Number:

CaltechAUTHORS:20200513-150749013

Persistent URL:

https://resolver.caltech.edu/CaltechAUTHORS:20200513-150749013

Official Citation:

Phosphine-catalyzed asymmetric additions of malonate esters to γ-substituted allenoates and allenamides. Riccardo Sinisi, Jianwei Sun, Gregory C. Fu. Proceedings of the National Academy of Sciences Nov 2010, 107 (48) 20652-20654; DOI: 10.1073/pnas.1003597107

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ID Code:

103188

Collection:

CaltechAUTHORS

Deposited By:

Tony Diaz

Deposited On:

13 May 2020 22:17

Last Modified:

16 Nov 2021 18:19

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