Stereoselective Construction of Fluorinated Quaternary Stereogenic Centers via an Organocatalytic Asymmetric exo-Selective Diels-Alder Reaction in the Presence of Water

Bojan P. Bondzić; Konstantinos Daskalakis; Tohru Taniguchi; Kenji Monde; Yujiro Hayashi

doi:10.1021/acs.orglett.2c03043

Stereoselective Construction of Fluorinated Quaternary Stereogenic Centers via an Organocatalytic Asymmetric exo-Selective Diels-Alder Reaction in the Presence of Water

Bojan P. Bondzić, Konstantinos Daskalakis, Tohru Taniguchi, Kenji Monde, Yujiro Hayashi

SCI - Chemistry

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

Abstract

A catalytic, asymmetric Diels-Alder reaction of α-fluoro α,β-unsaturated aldehydes and cyclopentadiene was developed using diarylprolinol silyl ether as an organocatalyst. The reaction proceeds in toluene with trifluoroacetic acid as an additive (condition A). Perchloric acid salt of diarylprolinol silyl ether also promotes the reaction using water as a reaction medium (condition B). In both cases, excellent exo-selectivity and enantioselectivity were obtained with generation of a fluorinated quaternary chiral center.

Original language	English
Pages (from-to)	7455-7460
Number of pages	6
Journal	Organic letters
Volume	24
Issue number	40
DOIs	https://doi.org/10.1021/acs.orglett.2c03043
Publication status	Published - 2022 Oct 14

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.2c03043

Cite this

Stereoselective Construction of Fluorinated Quaternary Stereogenic Centers via an Organocatalytic Asymmetric exo-Selective Diels-Alder Reaction in the Presence of Water. / Bondzić, Bojan P.; Daskalakis, Konstantinos; Taniguchi, Tohru et al.

In: Organic letters, Vol. 24, No. 40, 14.10.2022, p. 7455-7460.

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

@article{cd7705baf3c84e61b7303b5eb8be5779,

title = "Stereoselective Construction of Fluorinated Quaternary Stereogenic Centers via an Organocatalytic Asymmetric exo-Selective Diels-Alder Reaction in the Presence of Water",

abstract = "A catalytic, asymmetric Diels-Alder reaction of α-fluoro α,β-unsaturated aldehydes and cyclopentadiene was developed using diarylprolinol silyl ether as an organocatalyst. The reaction proceeds in toluene with trifluoroacetic acid as an additive (condition A). Perchloric acid salt of diarylprolinol silyl ether also promotes the reaction using water as a reaction medium (condition B). In both cases, excellent exo-selectivity and enantioselectivity were obtained with generation of a fluorinated quaternary chiral center.",

author = "Bondzi{\'c}, {Bojan P.} and Konstantinos Daskalakis and Tohru Taniguchi and Kenji Monde and Yujiro Hayashi",

note = "Funding Information: This work was supported by the Ministry of Education, Science and Technology of the Republic of Serbia (Grant 172020 to B.P.B.). This work was supported by JSPS KAKENHI Grant JP19H05630 (Y.H.). Publisher Copyright: {\textcopyright} 2022 American Chemical Society.",

year = "2022",

month = oct,

day = "14",

doi = "10.1021/acs.orglett.2c03043",

language = "English",

volume = "24",

pages = "7455--7460",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "40",

}

TY - JOUR

T1 - Stereoselective Construction of Fluorinated Quaternary Stereogenic Centers via an Organocatalytic Asymmetric exo-Selective Diels-Alder Reaction in the Presence of Water

AU - Bondzić, Bojan P.

AU - Daskalakis, Konstantinos

AU - Taniguchi, Tohru

AU - Monde, Kenji

AU - Hayashi, Yujiro

N1 - Funding Information: This work was supported by the Ministry of Education, Science and Technology of the Republic of Serbia (Grant 172020 to B.P.B.). This work was supported by JSPS KAKENHI Grant JP19H05630 (Y.H.). Publisher Copyright: © 2022 American Chemical Society.

PY - 2022/10/14

Y1 - 2022/10/14

N2 - A catalytic, asymmetric Diels-Alder reaction of α-fluoro α,β-unsaturated aldehydes and cyclopentadiene was developed using diarylprolinol silyl ether as an organocatalyst. The reaction proceeds in toluene with trifluoroacetic acid as an additive (condition A). Perchloric acid salt of diarylprolinol silyl ether also promotes the reaction using water as a reaction medium (condition B). In both cases, excellent exo-selectivity and enantioselectivity were obtained with generation of a fluorinated quaternary chiral center.

AB - A catalytic, asymmetric Diels-Alder reaction of α-fluoro α,β-unsaturated aldehydes and cyclopentadiene was developed using diarylprolinol silyl ether as an organocatalyst. The reaction proceeds in toluene with trifluoroacetic acid as an additive (condition A). Perchloric acid salt of diarylprolinol silyl ether also promotes the reaction using water as a reaction medium (condition B). In both cases, excellent exo-selectivity and enantioselectivity were obtained with generation of a fluorinated quaternary chiral center.

UR - http://www.scopus.com/inward/record.url?scp=85139421716&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85139421716&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.2c03043

DO - 10.1021/acs.orglett.2c03043

M3 - Article

C2 - 36190808

AN - SCOPUS:85139421716

SN - 1523-7060

VL - 24

SP - 7455

EP - 7460

JO - Organic Letters

JF - Organic Letters

IS - 40

ER -

Stereoselective Construction of Fluorinated Quaternary Stereogenic Centers via an Organocatalytic Asymmetric exo-Selective Diels-Alder Reaction in the Presence of Water

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this