Operationally Simple, Efficient, and Diastereoselective Synthesis of cis-2,6-Disubstituted-4-Methylene Tetrahydropyrans Catalyzed by Triflic Acid

Alessandra Puglisi; Ai-Lan Lee; Richard R. Schrock; Amir H. Hoveyda

doi:10.1021/ol060430f

Operationally Simple, Efficient, and Diastereoselective Synthesis of cis-2,6-Disubstituted-4-Methylene Tetrahydropyrans Catalyzed by Triflic Acid

Alessandra Puglisi, Ai-Lan Lee, Richard R. Schrock, Amir H. Hoveyda

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

26 Citations (Scopus)

Abstract

A highly efficient (0.01 mol % of TfOH), operationally simple (room temperature, inexpensive, and commercially available catalyst), and diastereoselective (up to >98% de) method for Brønsted acid-catalyzed reaction of enol ethers to form cis-2,6-disubstituted tetrahydropyrans is disclosed.

Original language	English
Pages (from-to)	1871-1874
Number of pages	4
Journal	Organic letters
Volume	8
Issue number	9
DOIs	https://doi.org/10.1021/ol060430f
Publication status	Published - 1 Apr 2006

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title = "Operationally Simple, Efficient, and Diastereoselective Synthesis of cis-2,6-Disubstituted-4-Methylene Tetrahydropyrans Catalyzed by Triflic Acid",

abstract = "A highly efficient (0.01 mol % of TfOH), operationally simple (room temperature, inexpensive, and commercially available catalyst), and diastereoselective (up to >98% de) method for Br{\o}nsted acid-catalyzed reaction of enol ethers to form cis-2,6-disubstituted tetrahydropyrans is disclosed.",

author = "Alessandra Puglisi and Ai-Lan Lee and Schrock, {Richard R.} and Hoveyda, {Amir H.}",

year = "2006",

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T1 - Operationally Simple, Efficient, and Diastereoselective Synthesis of cis-2,6-Disubstituted-4-Methylene Tetrahydropyrans Catalyzed by Triflic Acid

AU - Puglisi, Alessandra

AU - Lee, Ai-Lan

AU - Schrock, Richard R.

AU - Hoveyda, Amir H.

PY - 2006/4/1

Y1 - 2006/4/1

N2 - A highly efficient (0.01 mol % of TfOH), operationally simple (room temperature, inexpensive, and commercially available catalyst), and diastereoselective (up to >98% de) method for Brønsted acid-catalyzed reaction of enol ethers to form cis-2,6-disubstituted tetrahydropyrans is disclosed.

AB - A highly efficient (0.01 mol % of TfOH), operationally simple (room temperature, inexpensive, and commercially available catalyst), and diastereoselective (up to >98% de) method for Brønsted acid-catalyzed reaction of enol ethers to form cis-2,6-disubstituted tetrahydropyrans is disclosed.

U2 - 10.1021/ol060430f

DO - 10.1021/ol060430f

M3 - Article

SN - 1523-7060

VL - 8

SP - 1871

EP - 1874

JO - Organic letters

JF - Organic letters

IS - 9

ER -

Operationally Simple, Efficient, and Diastereoselective Synthesis of cis-2,6-Disubstituted-4-Methylene Tetrahydropyrans Catalyzed by Triflic Acid

Abstract

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