An organocascade approach to α,α-chlorofluoroalcohols

Montgomery D. Hayes; Melanie Rodríguez-Alvarado; Stacey E. Brenner-Moyer

doi:10.1016/j.tetlet.2015.05.107

An organocascade approach to α,α-chlorofluoroalcohols

Montgomery D. Hayes, Melanie Rodríguez-Alvarado, Stacey E. Brenner-Moyer

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

11 Scopus citations

Abstract

Abstract Fluorinated, tetrasubstituted, carbon stereocenters are challenging to install enantioselectively. gem-Chlorofluoro compounds contain a fluorinated, tetrasubstituted stereocenter, and are an entrée into other such compounds. We report herein the first catalytic, enantioselective method to prepare gem-chlorofluoro compounds from unfunctionalized aldehydes. This one-pot method precludes the isolation of volatile and/or reactive α-haloaldehyde intermediates.

Original language	English (US)
Article number	46379
Pages (from-to)	4718-4720
Number of pages	3
Journal	Tetrahedron Letters
Volume	56
Issue number	32
DOIs	https://doi.org/10.1016/j.tetlet.2015.05.107
State	Published - Jul 14 2015

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

Domino reactions
Fluorine
Organocatalysis
Synthetic method

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10.1016/j.tetlet.2015.05.107

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title = "An organocascade approach to α,α-chlorofluoroalcohols",

abstract = "Abstract Fluorinated, tetrasubstituted, carbon stereocenters are challenging to install enantioselectively. gem-Chlorofluoro compounds contain a fluorinated, tetrasubstituted stereocenter, and are an entr{\'e}e into other such compounds. We report herein the first catalytic, enantioselective method to prepare gem-chlorofluoro compounds from unfunctionalized aldehydes. This one-pot method precludes the isolation of volatile and/or reactive α-haloaldehyde intermediates.",

keywords = "Domino reactions, Fluorine, Organocatalysis, Synthetic method",

author = "Hayes, {Montgomery D.} and Melanie Rodr{\'i}guez-Alvarado and Brenner-Moyer, {Stacey E.}",

note = "Funding Information: This work was supported by the National Science Foundation ( CAREER-1148295 ) and the Alfred P. Sloan Foundation . The authors gratefully acknowledge Dr. Cliff Soll (City University of New York) and Dr. Furong Sun (University of Illinois) for the acquisition of mass spectrometry data, as well as Dr. William Brennessel (University of Rochester) for the acquisition of X-ray crystallographic data. The authors also thank Dr. Qunsheng Guo (Rutgers University) for his assistance completing the characterization of compound 11a . Publisher Copyright: {\textcopyright} 2015 Elsevier Ltd.",

year = "2015",

month = jul,

day = "14",

doi = "10.1016/j.tetlet.2015.05.107",

language = "English (US)",

volume = "56",

pages = "4718--4720",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - An organocascade approach to α,α-chlorofluoroalcohols

AU - Hayes, Montgomery D.

AU - Rodríguez-Alvarado, Melanie

AU - Brenner-Moyer, Stacey E.

N1 - Funding Information: This work was supported by the National Science Foundation ( CAREER-1148295 ) and the Alfred P. Sloan Foundation . The authors gratefully acknowledge Dr. Cliff Soll (City University of New York) and Dr. Furong Sun (University of Illinois) for the acquisition of mass spectrometry data, as well as Dr. William Brennessel (University of Rochester) for the acquisition of X-ray crystallographic data. The authors also thank Dr. Qunsheng Guo (Rutgers University) for his assistance completing the characterization of compound 11a . Publisher Copyright: © 2015 Elsevier Ltd.

PY - 2015/7/14

Y1 - 2015/7/14

N2 - Abstract Fluorinated, tetrasubstituted, carbon stereocenters are challenging to install enantioselectively. gem-Chlorofluoro compounds contain a fluorinated, tetrasubstituted stereocenter, and are an entrée into other such compounds. We report herein the first catalytic, enantioselective method to prepare gem-chlorofluoro compounds from unfunctionalized aldehydes. This one-pot method precludes the isolation of volatile and/or reactive α-haloaldehyde intermediates.

AB - Abstract Fluorinated, tetrasubstituted, carbon stereocenters are challenging to install enantioselectively. gem-Chlorofluoro compounds contain a fluorinated, tetrasubstituted stereocenter, and are an entrée into other such compounds. We report herein the first catalytic, enantioselective method to prepare gem-chlorofluoro compounds from unfunctionalized aldehydes. This one-pot method precludes the isolation of volatile and/or reactive α-haloaldehyde intermediates.

KW - Domino reactions

KW - Fluorine

KW - Organocatalysis

KW - Synthetic method

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U2 - 10.1016/j.tetlet.2015.05.107

DO - 10.1016/j.tetlet.2015.05.107

M3 - Article

AN - SCOPUS:84938211610

SN - 0040-4039

VL - 56

SP - 4718

EP - 4720

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 32

M1 - 46379

ER -

An organocascade approach to α,α-chlorofluoroalcohols

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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