Stereoselection in the Prins-pinacol synthesis of 2,2-disubstituted 4-acyltetrahydrofurans. Enantioselective synthesis of (-)-citreoviral

Naoyuki Hanaki; J. T. Link; David W.C. MacMillan; Larry E. Overman; William G. Trankle; Julie A. Wurster

doi:10.1021/ol991315q

Stereoselection in the Prins-pinacol synthesis of 2,2-disubstituted 4-acyltetrahydrofurans. Enantioselective synthesis of (-)-citreoviral

Naoyuki Hanaki, J. T. Link, David W.C. MacMillan, Larry E. Overman, William G. Trankle, Julie A. Wurster

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

58 Scopus citations

Abstract

(matrix presented) The condensation of allylic diols with unsymmetrical ketones proceeds with high stereoselection to form 2,2-disubstituted 4-acyltetrahydrofurans when the α-substituents of the ketone differ substantially in size. A Prins-pinacol condensation of this type is the central strategic step in an enantioselective synthesis of (-)-citreoviral.

Original language	English (US)
Pages (from-to)	223-226
Number of pages	4
Journal	Organic letters
Volume	2
Issue number	2
DOIs	https://doi.org/10.1021/ol991315q
State	Published - Jan 27 2000
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Stereoselection in the Prins-pinacol synthesis of 2,2-disubstituted 4-acyltetrahydrofurans. Enantioselective synthesis of (-)-citreoviral",

abstract = "(matrix presented) The condensation of allylic diols with unsymmetrical ketones proceeds with high stereoselection to form 2,2-disubstituted 4-acyltetrahydrofurans when the α-substituents of the ketone differ substantially in size. A Prins-pinacol condensation of this type is the central strategic step in an enantioselective synthesis of (-)-citreoviral.",

author = "Naoyuki Hanaki and Link, \{J. T.\} and MacMillan, \{David W.C.\} and Overman, \{Larry E.\} and Trankle, \{William G.\} and Wurster, \{Julie A.\}",

year = "2000",

month = jan,

day = "27",

doi = "10.1021/ol991315q",

language = "English (US)",

volume = "2",

pages = "223--226",

journal = "Organic letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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T1 - Stereoselection in the Prins-pinacol synthesis of 2,2-disubstituted 4-acyltetrahydrofurans. Enantioselective synthesis of (-)-citreoviral

AU - Hanaki, Naoyuki

AU - Link, J. T.

AU - MacMillan, David W.C.

AU - Overman, Larry E.

AU - Trankle, William G.

AU - Wurster, Julie A.

PY - 2000/1/27

Y1 - 2000/1/27

N2 - (matrix presented) The condensation of allylic diols with unsymmetrical ketones proceeds with high stereoselection to form 2,2-disubstituted 4-acyltetrahydrofurans when the α-substituents of the ketone differ substantially in size. A Prins-pinacol condensation of this type is the central strategic step in an enantioselective synthesis of (-)-citreoviral.

AB - (matrix presented) The condensation of allylic diols with unsymmetrical ketones proceeds with high stereoselection to form 2,2-disubstituted 4-acyltetrahydrofurans when the α-substituents of the ketone differ substantially in size. A Prins-pinacol condensation of this type is the central strategic step in an enantioselective synthesis of (-)-citreoviral.

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UR - https://www.scopus.com/inward/citedby.url?scp=0034719252&partnerID=8YFLogxK

U2 - 10.1021/ol991315q

DO - 10.1021/ol991315q

M3 - Article

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VL - 2

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JO - Organic letters

JF - Organic letters

IS - 2

ER -

Stereoselection in the Prins-pinacol synthesis of 2,2-disubstituted 4-acyltetrahydrofurans. Enantioselective synthesis of (-)-citreoviral

Abstract

All Science Journal Classification (ASJC) codes

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