Stereoselection in the prins-pinacol synthesis of acyltetrahydrofurans

Frederick Cohen; David W.C. MacMillan; Larry E. Overman; Alex Romero

doi:10.1021/ol0157003

Stereoselection in the prins-pinacol synthesis of acyltetrahydrofurans

Frederick Cohen, David W.C. MacMillan, Larry E. Overman, Alex Romero

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

41 Scopus citations

Abstract

Matrix presented Depending upon the nature of the alkene and allylic substituents, acid-promoted rearrangements of acetals derived from anti allylic diols give 12 or stereoisomeric acyltetrahydrofurans 13. Stereoelectronic effects of the allylic substituents and the extent of bonding in the Prins cyclization transition state are central features of a proposed new model for predicting stereoselection in the Prins-pinacol synthesis of acyltetrahydrofurans.

Original language	English (US)
Pages (from-to)	1225-1228
Number of pages	4
Journal	Organic letters
Volume	3
Issue number	8
DOIs	https://doi.org/10.1021/ol0157003
State	Published - Apr 19 2001
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol0157003

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abstract = "Matrix presented Depending upon the nature of the alkene and allylic substituents, acid-promoted rearrangements of acetals derived from anti allylic diols give 12 or stereoisomeric acyltetrahydrofurans 13. Stereoelectronic effects of the allylic substituents and the extent of bonding in the Prins cyclization transition state are central features of a proposed new model for predicting stereoselection in the Prins-pinacol synthesis of acyltetrahydrofurans.",

author = "Frederick Cohen and MacMillan, {David W.C.} and Overman, {Larry E.} and Alex Romero",

year = "2001",

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AU - Cohen, Frederick

AU - MacMillan, David W.C.

AU - Overman, Larry E.

AU - Romero, Alex

PY - 2001/4/19

Y1 - 2001/4/19

N2 - Matrix presented Depending upon the nature of the alkene and allylic substituents, acid-promoted rearrangements of acetals derived from anti allylic diols give 12 or stereoisomeric acyltetrahydrofurans 13. Stereoelectronic effects of the allylic substituents and the extent of bonding in the Prins cyclization transition state are central features of a proposed new model for predicting stereoselection in the Prins-pinacol synthesis of acyltetrahydrofurans.

AB - Matrix presented Depending upon the nature of the alkene and allylic substituents, acid-promoted rearrangements of acetals derived from anti allylic diols give 12 or stereoisomeric acyltetrahydrofurans 13. Stereoelectronic effects of the allylic substituents and the extent of bonding in the Prins cyclization transition state are central features of a proposed new model for predicting stereoselection in the Prins-pinacol synthesis of acyltetrahydrofurans.

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Stereoselection in the prins-pinacol synthesis of acyltetrahydrofurans

Abstract

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