Atom efficient synthesis of selectively difluorinated carbocycles through a gold(I) catalyzed cyclization

Adam W. McCarter; Magdalana Sommer; Jonathan M. Percy; Craig Jamieson; Alan R. Kennedy; David J. Hirst

doi:10.1021/acs.joc.8b01121

Atom efficient synthesis of selectively difluorinated carbocycles through a gold(I) catalyzed cyclization

Adam W. McCarter, Magdalana Sommer, Jonathan M. Percy, Craig Jamieson, Alan R. Kennedy, David J. Hirst

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

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Abstract

The intramolecular carbocyclization of difluorinated enol acetals has been achieved for the first time using gold(I) catalysis. Difluorinated enol acetals bearing a pendant alkene group can be cyclized and reduced in one pot to form fluorinated diol motifs. Alternatively, the cyclization of terminal alkynes allows for the synthesis of fluorinated pyran scaffolds. Both cyclization processes can be performed under mild conditions allowing access to complex products rich in functionality. The cyclic systems are synthesized concisely (maximum four steps) from trifluoroethanol, an inexpensive fluorinated feedstock.

Original language	English
Journal	Journal of Organic Chemistry
Early online date	6 Jul 2018
DOIs	https://doi.org/10.1021/acs.joc.8b01121
Publication status	E-pub ahead of print - 6 Jul 2018

Keywords

gold(I) catalysis
cyclization processes
synthesis

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10.1021/acs.joc.8b01121

McCarter-etal-JOC-2018-Atom-efficient-synthesis-of-selectively-difluorinated-carbocyclesAccepted author manuscript, 1.6 MB

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title = "Atom efficient synthesis of selectively difluorinated carbocycles through a gold(I) catalyzed cyclization",

abstract = "The intramolecular carbocyclization of difluorinated enol acetals has been achieved for the first time using gold(I) catalysis. Difluorinated enol acetals bearing a pendant alkene group can be cyclized and reduced in one pot to form fluorinated diol motifs. Alternatively, the cyclization of terminal alkynes allows for the synthesis of fluorinated pyran scaffolds. Both cyclization processes can be performed under mild conditions allowing access to complex products rich in functionality. The cyclic systems are synthesized concisely (maximum four steps) from trifluoroethanol, an inexpensive fluorinated feedstock.",

keywords = "gold(I) catalysis, cyclization processes, synthesis",

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T1 - Atom efficient synthesis of selectively difluorinated carbocycles through a gold(I) catalyzed cyclization

AU - McCarter, Adam W.

AU - Sommer, Magdalana

AU - Percy, Jonathan M.

AU - Jamieson, Craig

AU - Kennedy, Alan R.

AU - Hirst, David J.

PY - 2018/7/6

Y1 - 2018/7/6

N2 - The intramolecular carbocyclization of difluorinated enol acetals has been achieved for the first time using gold(I) catalysis. Difluorinated enol acetals bearing a pendant alkene group can be cyclized and reduced in one pot to form fluorinated diol motifs. Alternatively, the cyclization of terminal alkynes allows for the synthesis of fluorinated pyran scaffolds. Both cyclization processes can be performed under mild conditions allowing access to complex products rich in functionality. The cyclic systems are synthesized concisely (maximum four steps) from trifluoroethanol, an inexpensive fluorinated feedstock.

AB - The intramolecular carbocyclization of difluorinated enol acetals has been achieved for the first time using gold(I) catalysis. Difluorinated enol acetals bearing a pendant alkene group can be cyclized and reduced in one pot to form fluorinated diol motifs. Alternatively, the cyclization of terminal alkynes allows for the synthesis of fluorinated pyran scaffolds. Both cyclization processes can be performed under mild conditions allowing access to complex products rich in functionality. The cyclic systems are synthesized concisely (maximum four steps) from trifluoroethanol, an inexpensive fluorinated feedstock.

KW - gold(I) catalysis

KW - cyclization processes

KW - synthesis

UR - https://pubs.acs.org/journal/joceah

U2 - 10.1021/acs.joc.8b01121

DO - 10.1021/acs.joc.8b01121

M3 - Article

SN - 0022-3263

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

ER -

Atom efficient synthesis of selectively difluorinated carbocycles through a gold(I) catalyzed cyclization

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Keywords

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