Stereoselective synthesis of styrene oxides via a Mitsunobu cyclodehydration

Steven A. Weissman; Kai Rossen; Paul J. Reider

doi:10.1021/ol016167u

Stereoselective synthesis of styrene oxides via a Mitsunobu cyclodehydration

Steven A. Weissman, Kai Rossen, Paul J. Reider

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45 Scopus citations

Abstract

(Equation presented) The Mitsunobu cyclodehydration of chiral phenethane-1,2-diols (4), readily accessed from the styrene derivative (5), has been demonstrated to provide the corresponding styrene oxides (2) with high levels of stereoretention (up to 99%) Optimized reaction conditions are described, from which the combination of tricyclohexylphosphine (Chx₃P) and diisopropylazodicarboxylate (DIAD) in THF and R = EWG provides the best results.

Original language	English (US)
Pages (from-to)	2513-2515
Number of pages	3
Journal	Organic letters
Volume	3
Issue number	16
DOIs	https://doi.org/10.1021/ol016167u
State	Published - Aug 9 2001
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol016167u

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title = "Stereoselective synthesis of styrene oxides via a Mitsunobu cyclodehydration",

abstract = "(Equation presented) The Mitsunobu cyclodehydration of chiral phenethane-1,2-diols (4), readily accessed from the styrene derivative (5), has been demonstrated to provide the corresponding styrene oxides (2) with high levels of stereoretention (up to 99%) Optimized reaction conditions are described, from which the combination of tricyclohexylphosphine (Chx3P) and diisopropylazodicarboxylate (DIAD) in THF and R = EWG provides the best results.",

author = "Weissman, {Steven A.} and Kai Rossen and Reider, {Paul J.}",

year = "2001",

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doi = "10.1021/ol016167u",

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journal = "Organic letters",

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T1 - Stereoselective synthesis of styrene oxides via a Mitsunobu cyclodehydration

AU - Weissman, Steven A.

AU - Rossen, Kai

AU - Reider, Paul J.

PY - 2001/8/9

Y1 - 2001/8/9

N2 - (Equation presented) The Mitsunobu cyclodehydration of chiral phenethane-1,2-diols (4), readily accessed from the styrene derivative (5), has been demonstrated to provide the corresponding styrene oxides (2) with high levels of stereoretention (up to 99%) Optimized reaction conditions are described, from which the combination of tricyclohexylphosphine (Chx3P) and diisopropylazodicarboxylate (DIAD) in THF and R = EWG provides the best results.

AB - (Equation presented) The Mitsunobu cyclodehydration of chiral phenethane-1,2-diols (4), readily accessed from the styrene derivative (5), has been demonstrated to provide the corresponding styrene oxides (2) with high levels of stereoretention (up to 99%) Optimized reaction conditions are described, from which the combination of tricyclohexylphosphine (Chx3P) and diisopropylazodicarboxylate (DIAD) in THF and R = EWG provides the best results.

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JO - Organic letters

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ER -

Stereoselective synthesis of styrene oxides via a Mitsunobu cyclodehydration

Abstract

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