Elimination versus Ring Opening: A Convergent Route to Allrylidene-Cyclobutanes

被引：22

作者：

Brioche, Julien ^{[1
]}

Michalak, Michal ^{[1
]}

Quiclet-Sire, Beatrice ^{[1
]}

Zard, Samir Z. ^{[1
]}

机构：

[1] Ecole Polytech, CNRS, UMR 7652, Synth Organ Lab, F-91128 Palaiseau, France

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 23期

关键词：

ENANTIOSELECTIVE SYNTHESIS; RADICAL-ADDITION; ACCESS; DERIVATIVES; EXPANSION; METHYLENECYCLOBUTANES; OLEFINS; CARBON; CYCLOADDITION; KINETICS;

D O I：

10.1021/ol202798r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Functionalized alkylidene-cyclobutanes have been prepared from 2-fluoropyridinyl-6-oxy precursors derived from vinyl cyclobutanols by a radical addition elimination process. A wide range of functional groups is tolerated, and the alkylidene-cyclobutanes can be further elaborated Into cyclopentanones. The limitation of this approach resides in the competition with opening of the cyclobutane ring.

引用

页码：6296 / 6299

页数：4

共 52 条

[1] THE KINETICS AND MECHANISM OF RING-OPENING OF RADICALS CONTAINING THE CYCLOBUTYLCARBINYL SYSTEM [J].

BECKWITH, ALJ ;

MOAD, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1980, (07) :1083-1092

[2] A highly stereocontrolled formal total synthesis of (±)- and of (-)-grandisol by 1,4-conjugated addition of organocopper reagents to cyclobutylidene derivatives [J].

Bernard, Angela M. ;

Frongia, Angelo ;

Ollivier, Jean ;

Piras, Pier Paolo ;

Secci, Francesco ;

Spiga, Marco .

TETRAHEDRON, 2007, 63 (23) :4968-4974

[3] L-proline-catalyzed direct intermolecular asymmetric aldol reactions of 1-phenylthiocycloalkyl carboxaldehydes with ketones. Easy access to spiro- and fused-cyclobutyl tetrahydrofurans and cyclopentanones [J].

Bernard, Angela M. ;

Frongia, Angelo ;

Guillot, Regis ;

Piras, Pier P. ;

Secci, Francesco ;

Spiga, Marco .

ORGANIC LETTERS, 2007, 9 (03) :541-544

[4] Intermolecular additions of cyclobutanone derived radicals. A convergent, highly efficient access to polycyclic cyclobutane containing structures [J].

Binot, G ;

Zard, SZ .

TETRAHEDRON LETTERS, 2003, 44 (42) :7703-7706

[5] PALLADIUM(II)-CATALYZED RING EXPANSION OF METHYLENECYCLOBUTANES AND RELATED SYSTEMS [J].

BOONTANONDA, P ;

GRIGG, R .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (17) :583-584

[6] A Highly Stereoselective, Modular Route to (E)-Vinylsulfones and to (Z)- and (E)-Alkenes [J].

Braun, Marie-Gabrielle ;

Quiclet-Sire, Beatrice ;

Zard, Samir Z. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (40) :15954-15957

[7] SYNTHESIS OF 3-HYDROXY-3-CYCLOBUTENE-1,2-DIONE BASED AMINO-ACIDS [J].

CAMPBELL, EF ;

PARK, AK ;

KINNEY, WA ;

FENGL, RW ;

LIEBESKIND, LS .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (05) :1470-1472

[8] Allylic alcohols as radical allylating agents. An overall olefination of aldehydes and ketones [J].

Charrier, Nicolas ;

Quiclet-Sire, Beatrice ;

Zard, Samir Z. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (28) :8898-+

[9] Laser flash photolysis measurements of the kinetics of ring opening of the 2,2-diphenylcyclobutylcarbinyl radical [J].

Choi, SY ;

Horner, JH ;

Newcomb, M .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (14) :4447-4449

[10] Asymmetric synthesis of enantiomerically enriched atropisomeric amides by desymmetrisation of N,N-dialkylmesitamides [J].

Clayden, J ;

Johnson, P ;

Pink, JH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (04) :371-375

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