Synthesis of Phthalans Via Copper-Catalyzed Enantioselective Cyclization/Carboetherification of 2-Vinylbenzyl Alcohols

Dake Chen; Sherry R. Chemler

doi:10.1021/acs.orglett.8b02766

Synthesis of Phthalans Via Copper-Catalyzed Enantioselective Cyclization/Carboetherification of 2-Vinylbenzyl Alcohols

Dake Chen
, Sherry R. Chemler

Chemistry

SUNY Buffalo

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

29 Scopus citations

Abstract

Enantiomerically enriched phthalans were synthesized efficiently via an enantioselective copper-catalyzed alkene carboetherification reaction. In this reaction, 2-vinylbenzyl alcohols enantioselectively cyclize then couple with vinylarenes. The utility of the method was demonstrated by the enantioselective synthesis of (R)-fluspidine, a σ₁ receptor ligand.

Original language	English
Pages (from-to)	6453-6456
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	20
DOIs	https://doi.org/10.1021/acs.orglett.8b02766
State	Published - Oct 19 2018

Access to Document

10.1021/acs.orglett.8b02766

Cite this

@article{78cb4b274fee43ecb8a1a4cc31b00a37,

title = "Synthesis of Phthalans Via Copper-Catalyzed Enantioselective Cyclization/Carboetherification of 2-Vinylbenzyl Alcohols",

abstract = "Enantiomerically enriched phthalans were synthesized efficiently via an enantioselective copper-catalyzed alkene carboetherification reaction. In this reaction, 2-vinylbenzyl alcohols enantioselectively cyclize then couple with vinylarenes. The utility of the method was demonstrated by the enantioselective synthesis of (R)-fluspidine, a σ1 receptor ligand.",

author = "Dake Chen and Chemler, \{Sherry R.\}",

note = "Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

month = oct,

day = "19",

doi = "10.1021/acs.orglett.8b02766",

language = "English",

volume = "20",

pages = "6453--6456",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "20",

}

TY - JOUR

T1 - Synthesis of Phthalans Via Copper-Catalyzed Enantioselective Cyclization/Carboetherification of 2-Vinylbenzyl Alcohols

AU - Chen, Dake

AU - Chemler, Sherry R.

PY - 2018/10/19

Y1 - 2018/10/19

N2 - Enantiomerically enriched phthalans were synthesized efficiently via an enantioselective copper-catalyzed alkene carboetherification reaction. In this reaction, 2-vinylbenzyl alcohols enantioselectively cyclize then couple with vinylarenes. The utility of the method was demonstrated by the enantioselective synthesis of (R)-fluspidine, a σ1 receptor ligand.

AB - Enantiomerically enriched phthalans were synthesized efficiently via an enantioselective copper-catalyzed alkene carboetherification reaction. In this reaction, 2-vinylbenzyl alcohols enantioselectively cyclize then couple with vinylarenes. The utility of the method was demonstrated by the enantioselective synthesis of (R)-fluspidine, a σ1 receptor ligand.

UR - https://www.scopus.com/pages/publications/85054922114

U2 - 10.1021/acs.orglett.8b02766

DO - 10.1021/acs.orglett.8b02766

M3 - Article

C2 - 30336677

AN - SCOPUS:85054922114

SN - 1523-7060

VL - 20

SP - 6453

EP - 6456

JO - Organic Letters

JF - Organic Letters

IS - 20

ER -

Synthesis of Phthalans Via Copper-Catalyzed Enantioselective Cyclization/Carboetherification of 2-Vinylbenzyl Alcohols

Abstract

Access to Document

Other files and links

Fingerprint

Cite this