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

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

47 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

Access to Document

10.1021/ol016167u

Cite this

@article{3477b2f440e6453595d45cc904acb949,

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",

month = aug,

day = "9",

doi = "10.1021/ol016167u",

language = "English (US)",

volume = "3",

pages = "2513--2515",

journal = "Organic letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "16",

}

TY - JOUR

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.

UR - https://www.scopus.com/pages/publications/0035833732

UR - https://www.scopus.com/pages/publications/0035833732#tab=citedBy

U2 - 10.1021/ol016167u

DO - 10.1021/ol016167u

M3 - Article

C2 - 11483048

AN - SCOPUS:0035833732

SN - 1523-7060

VL - 3

SP - 2513

EP - 2515

JO - Organic letters

JF - Organic letters

IS - 16

ER -

Stereoselective synthesis of styrene oxides via a Mitsunobu cyclodehydration

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this