Stereloselective cascade reactions that incorporate a 7-exo acyl radical cyclization

被引：33

作者：

Grant, SW ^{[1
]}

Zhu, KD ^{[1
]}

Zhang, Y ^{[1
]}

Castle, SL ^{[1
]}

机构：

[1] Brigham Young Univ, Dept Chem & Biochem, Provo, UT 84602 USA

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 09期

关键词：

D O I：

10.1021/ol0604264

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Radical cascades that feature a 7-exo acyl radical cyclization followed by a 6-exo or 5-exo alkyl radical cyclization proceed with very good yields and diastereoselectivities. Two stereocenters are created by the reaction, and a single isomeric product was obtained from each of the five substrates examined. The relative configurations of the products are consistent with cyclizations occurring via chairlike or pseudochairlike transition states.

引用

页码：1867 / 1870

页数：4

共 23 条

[1]

Boger DL, 1997, ISR J CHEM, V37, P119

[2] ACYL RADICALS - FUNCTIONALIZED FREE-RADICALS FOR INTRAMOLECULAR CYCLIZATION REACTIONS [J].

BOGER, DL ;

MATHVINK, RJ .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (14) :3377-3379

[3] ACYL RADICALS - INTERMOLECULAR AND INTRAMOLECULAR ALKENE ADDITION-REACTIONS [J].

BOGER, DL ;

MATHVINK, RJ .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (05) :1429-1443

[4] Chemistry of acyl radicals [J].

Chatgilialoglu, C ;

Crich, D ;

Komatsu, M ;

Ryu, I .

CHEMICAL REVIEWS, 1999, 99 (08) :1991-2069

[5] Stereoselective construction of trans-disubstituted azabicycles using oxauracil as a novel free radical acceptor [J].

Evans, PA ;

Manangan, T ;

Rheingold, AL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (44) :11009-11010

[6] Intramolecular addition of acyl radicals to α-substituted vinylogous carbonates:: demonstrating the effect of ring size on acyclic stereocontrol [J].

Evans, PA ;

Raina, S ;

Ahsan, K .

CHEMICAL COMMUNICATIONS, 2001, (23) :2504-2505

[7] Vinylogous sulfonates as radical acceptors for the stereoselective synthesis of cyclic ethers [J].

Evans, PA ;

Manangan, T .

TETRAHEDRON LETTERS, 1997, 38 (47) :8165-8168

[8] Stereoselective synthesis of cyclic ethers using vinylogous sulfonates as radical accepters:: Effect of E/Z geometry and temperature on diastereoselectivity [J].

Evans, PA ;

Manangan, T .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (15) :4523-4528

[9] Stereoselective construction of cyclic ethers via intramolecular acyl radical cyclizations: A practical solution to decarbonylation [J].

Evans, PA ;

Roseman, JD .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (07) :2252-2253

[10] CATION-STABILIZING AUXILIARIES IN POLYENE CYCLIZATIONS .7. THE FLUORINE ATOM AS A CATION-STABILIZING AUXILIARY IN BIOMIMETIC POLYENE CYCLIZATIONS .4. TOTAL SYNTHESIS OF DL-BETA-AMYRIN [J].

JOHNSON, WS ;

PLUMMER, MS ;

REDDY, SP ;

BARTLETT, WR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (02) :515-521

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