Synthesis of 1,3-dihydrobenzo[c]furans from ortho-lithiated aryloxiranes

被引：28

作者：

Capriati, V ^{[1
]}

Florio, S ^{[1
]}

Luisi, R ^{[1
]}

Perna, FM ^{[1
]}

Salomone, A ^{[1
]}

机构：

[1] Univ Bari, Dipartimento Farmacochim, CNR, ICCOM,Sez Bari, I-70125 Bari, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 10期

关键词：

D O I：

10.1021/jo052645t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general method for the synthesis of hydroxyalkyl 1,3-dihydrobenzo[c] furans from ortho-lithiated aryloxiranes and carbonyl compounds is described.

引用

页码：3984 / 3987

页数：4

共 21 条

[1] RULES FOR RING-CLOSURE [J].

BALDWIN, JE .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :734-736

[2] The formation and stabillity of spiro-compounds. Part I. Spiro-compounds from cyclo-hexane. [J].

Beesley, RM ;

Ingold, CK ;

Thorpe, JF .

JOURNAL OF THE CHEMICAL SOCIETY, 1915, 107 :1080-1106

[3] An efficient route to tetrahydronaphthols via addition of ortho-lithiated stilbene oxides to α,β-unsaturated Fischer carbene complexes [J].

Capriati, V ;

Florio, S ;

Luisi, R ;

Perna, FM ;

Salomone, A ;

Gasparrini, F .

ORGANIC LETTERS, 2005, 7 (22) :4895-4898

[4] Directed ortho lithiation of N-alkylphenylaziridines [J].

Capriati, V ;

Florio, S ;

Luisi, R ;

Musio, B .

ORGANIC LETTERS, 2005, 7 (17) :3749-3752

[5] Metalated heterocycles and their applications in synthetic organic chemistry [J].

Chinchilla, R ;

Nájera, C ;

Yus, M .

CHEMICAL REVIEWS, 2004, 104 (05) :2667-2722

[6]

COOTE SJ, 1989, J ORGANOMET CHEM, V37, P81

[7] Preparation of functionalized arylmagnesium reagents bearing an o-chloromethyl group [J].

Delacroix, T ;

Bérillon, L ;

Cahiez, G ;

Knochel, P .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (23) :8108-8110

[8] Facile separation of chiral 1,3-dihydrobenzo[c]furan derivatives using a D-xylose moiety as a protecting group [J].

Ewing, DF ;

Len, C ;

Mackenzie, G ;

Ronco, G ;

Villa, P .

TETRAHEDRON-ASYMMETRY, 2000, 11 (24) :4995-5002

[9] A new method for benzylic deprotonative lithiation: synthesis of 1-and 1,3-disubstituted (aza)phthalans [J].

Fort, Y ;

Gros, P ;

Rodriguez, AL .

TETRAHEDRON LETTERS, 2002, 43 (22) :4045-4048

[10] The conditions underlying the formation of unsaturated and of cyclic compounds from halogenated open-chain derivatives Part I Products derived from a-halogenated glutaric acids [J].

Ingold, CK .

JOURNAL OF THE CHEMICAL SOCIETY, 1921, 119 :305-329

← 1 2 3 →