Enantiopure cis- and trans-2,5-disubstituted-2,5-dihydrofurans from D-allal- and D-galactal-derived vinyl epoxides

被引：2

作者：

Di Bussolo, Valeria ^{[1
]}

Princiotto, Salvatore ^{[2
,3
]}

Bordoni, Vittorio ^{[2
,4
]}

Martinelli, Elisa ^{[2
]}

Favero, Lucilla ^{[2
]}

Crotti, Stefano ^{[2
,5
]}

Uccello-Barretta, Gloria ^{[1
]}

Balzano, Federica ^{[1
]}

Pineschi, Mauro ^{[2
]}

Crotti, Paolo ^{[2
]}

机构：

[1] Univ Pisa, Dipartimento Chim & Chim Ind, Via G Moruzzi 3, I-56124 Pisa, Italy

[2] Univ Pisa, Dipartimento Farm, Via Bonanno 33, I-56126 Pisa, Italy

[3] Univ Siena, Dipartimento Biotecnol Chim & Farm, Via Aldo Moro 2, I-53100 Siena, Italy

[4] Max Planck Inst Colloids & Interfaces, Muhlenberg 1, D-14476 Potsdam, Germany

[5] Kedrion Biopharma, Lucca, Italy

来源：

TETRAHEDRON | 2019年 / 75卷 / 33期

关键词：

Vinyl epoxides; Glycals; 2,5-Disubstituted-2,5-dihydrofurans; Rearrangement process; Stereoselectivity; COUPLING-CYCLIZATION REACTION; RING-CLOSING METATHESIS; STEREOSELECTIVE-SYNTHESIS; SUBSTITUTED 2,5-DIHYDROFURAN; CATALYZED CYCLIZATION; NUCLEOPHILIC-ADDITION; EFFICIENT SYNTHESIS; C-GLYCOSIDATION; O-GLYCOSYLATION; HECK REACTION;

D O I：

10.1016/j.tet.2019.06.003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Upon treatment with the metal enolates of methylene active compounds (dimethyl malonate and dibenzoylmethane) (C-nucleophiles) and benzyl carbamate (N-nucleophile), D-allal- and D-galactal-derived vinyl epoxides are stereoselectively transformed, in a single step, into diastereoisomeric, highly functionalized, enantiopure cis- and trans-2,5-disubstituted-2,5-dihydrofurans. (C) 2019 Elsevier Ltd. All rights reserved.

引用

页码：4425 / 4443

页数：19

共 6 条

[1] Enantiopure Cis-2,5-Disubstituted 2,5-Dihydropyrroles from D-Glycal-Derived Vinyl Aziridines
Di Bussolo, Valeria
Frau, Ileana
Crotti, Stefano
Uccello-Barretta, Gloria
Balzano, Federica
Pineschi, Mauro
Crotti, Paolo
ORGANIC LETTERS, 2013, 15 (23) : 6026 - 6029
[2] Synthesis of carba analogs of 6-O-(benzyl)-D-allal- and -D-galactal-derived allyl epoxides and evaluation of the regio- and stereoselective behavior in nucleophilic addition reactions
Di Bussolo, Valeria
Frau, Ileana
Checchia, Lorenzo
Favero, Lucilla
Pineschi, Mauro
Uccello-Barretta, Gloria
Balzano, Federica
Roselli, Graziella
Renzi, Gabriele
Crotti, Paolo
TETRAHEDRON, 2011, 67 (25) : 4696 - 4709
[3] D-Allal- and D-Galactal-Derived Vinyl N-Mesylaziridines: Regio- and Stereoselectivity in Addition Reactions of O-, C-, N-, and S-Nucleophiles
Di Bussolo, Valeria
Frau, Ileana
Pineschi, Mauro
Crotti, Paolo
SYNTHESIS-STUTTGART, 2012, 44 (18): : 2863 - 2871
[4] ENANTIOENRICHED FORMATION OF SYNTHONS OF 1,5-HEXADIENE BIS-EPOXIDES FOR CONSTRUCTION OF NONRACEMIC CIS- AND TRANS-2,5-DISUBSTITUTED TETRAHYDROFURANS
Williams, David R.
De, Ramkrishna
HETEROCYCLES, 2012, 84 (01) : 385 - 391
[5] Asymmetric Synthesis of cis- and trans-2,5-disubstituted pyrrolidines from 3-oxo pyrrolidine 2-phosphonates:: Synthesis of (+)-preussin and analogs
Davis, Franklin A.
Zhang, Junyi
Qiu, Hui
Wu, Yongzhong
ORGANIC LETTERS, 2008, 10 (07) : 1433 - 1436
[6] Synthesis and ring-opening reactions of the diastereoisomeric cis- and trans-epoxides derived from 3-(benzyloxy)cyclopentene and 2-(benzyloxy)-2,5-dihydrofuran
Crotti, P
Di Bussolo, V
Favero, L
Macchia, F
Pineschi, M
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1998, 1998 (08) : 1675 - 1686

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