Organocatalytic, Enantioselective Synthesis of 1- and 3-Substituted Isochromans via Intramolecular Oxa-Michael Reaction of Alkoxyboronate: Synthesis of (+)-Sonepiprazole

Barnala Ravindra; Sanjay Maity; Braja Gopal Das; Prasanta Ghorai

doi:10.1021/acs.joc.5b00719

Organocatalytic, Enantioselective Synthesis of 1- and 3-Substituted Isochromans via Intramolecular Oxa-Michael Reaction of Alkoxyboronate: Synthesis of (+)-Sonepiprazole

Barnala Ravindra, Sanjay Maity, Braja Gopal Das, Prasanta Ghorai

Chemistry (Twin Cities)

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

41 Scopus citations

Abstract

The enantioselective oxa-Michael reaction of alkoxyboronate strategy was demonstrated to provide a new and practical route to enantioriched 1- and 3-substituted isochromans using a chiral bifunctional organocatalyst. Furthermore, this methodology was extended to the enantioselective synthesis of (+)-sonepiprazole, a dopamine receptor antagonist.

Original language	English (US)
Pages (from-to)	7008-7018
Number of pages	11
Journal	Journal of Organic Chemistry
Volume	80
Issue number	14
DOIs	https://doi.org/10.1021/acs.joc.5b00719
State	Published - Jul 17 2015

Bibliographical note

Publisher Copyright:
© 2015 American Chemical Society.

Publisher link

10.1021/acs.joc.5b00719

Find It

Find It at U of M Libraries

Cite this

Organocatalytic, Enantioselective Synthesis of 1- and 3-Substituted Isochromans via Intramolecular Oxa-Michael Reaction of Alkoxyboronate: Synthesis of (+)-Sonepiprazole. / Ravindra, Barnala; Maity, Sanjay; Das, Braja Gopal et al.
In: Journal of Organic Chemistry, Vol. 80, No. 14, 17.07.2015, p. 7008-7018.

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

@article{8b6a4199114a47ea94f5fa2438008a76,

title = "Organocatalytic, Enantioselective Synthesis of 1- and 3-Substituted Isochromans via Intramolecular Oxa-Michael Reaction of Alkoxyboronate: Synthesis of (+)-Sonepiprazole",

abstract = "The enantioselective oxa-Michael reaction of alkoxyboronate strategy was demonstrated to provide a new and practical route to enantioriched 1- and 3-substituted isochromans using a chiral bifunctional organocatalyst. Furthermore, this methodology was extended to the enantioselective synthesis of (+)-sonepiprazole, a dopamine receptor antagonist.",

author = "Barnala Ravindra and Sanjay Maity and Das, {Braja Gopal} and Prasanta Ghorai",

note = "Publisher Copyright: {\textcopyright} 2015 American Chemical Society.",

year = "2015",

month = jul,

day = "17",

doi = "10.1021/acs.joc.5b00719",

language = "English (US)",

volume = "80",

pages = "7008--7018",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "14",

}

TY - JOUR

T1 - Organocatalytic, Enantioselective Synthesis of 1- and 3-Substituted Isochromans via Intramolecular Oxa-Michael Reaction of Alkoxyboronate

T2 - Synthesis of (+)-Sonepiprazole

AU - Ravindra, Barnala

AU - Maity, Sanjay

AU - Das, Braja Gopal

AU - Ghorai, Prasanta

PY - 2015/7/17

Y1 - 2015/7/17

N2 - The enantioselective oxa-Michael reaction of alkoxyboronate strategy was demonstrated to provide a new and practical route to enantioriched 1- and 3-substituted isochromans using a chiral bifunctional organocatalyst. Furthermore, this methodology was extended to the enantioselective synthesis of (+)-sonepiprazole, a dopamine receptor antagonist.

AB - The enantioselective oxa-Michael reaction of alkoxyboronate strategy was demonstrated to provide a new and practical route to enantioriched 1- and 3-substituted isochromans using a chiral bifunctional organocatalyst. Furthermore, this methodology was extended to the enantioselective synthesis of (+)-sonepiprazole, a dopamine receptor antagonist.

UR - http://www.scopus.com/inward/record.url?scp=84937605883&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84937605883&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.5b00719

DO - 10.1021/acs.joc.5b00719

M3 - Article

C2 - 26102523

AN - SCOPUS:84937605883

SN - 0022-3263

VL - 80

SP - 7008

EP - 7018

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 14

ER -

Organocatalytic, Enantioselective Synthesis of 1- and 3-Substituted Isochromans via Intramolecular Oxa-Michael Reaction of Alkoxyboronate: Synthesis of (+)-Sonepiprazole

Abstract

Bibliographical note

Publisher link

Find It

Other files and links

Fingerprint

Cite this