Superbase-promoted rearrangement of oxiranes to cyclopropanes

被引：18

作者：

Mordini, A ^{[1
]}

Peruzzi, D ^{[1
]}

Russo, F ^{[1
]}

Valacchi, M ^{[1
]}

Reginato, G ^{[1
]}

Brandi, A ^{[1
]}

机构：

[1] Ist Chim Composti Organomet, Dipartimento Chim Organ U Schiff, I-50019 Florence, Italy

来源：

TETRAHEDRON | 2005年 / 61卷 / 13期

关键词：

superbase; cyclopropanes; rearrangement; 3-exo cyclization;

D O I：

10.1016/j.tet.2005.01.102

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aryl- and alkenyl substituted oxiranes, when submitted to treatment with superbasic reagents, undergo a highly regio- and stereoselective rearrangement leading to cyclopropyl methanol derivatives. The process can also be applied to mono- and dihydroxy substituted substrates thus leading to polyhydroxylated cyclopropanes. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：3349 / 3360

页数：12

共 42 条

[1] Enantioselective synthesis of (S)-Vigabatrin(R) [J].

Alcon, M ;

Poch, M ;

Moyano, A ;

Pericas, MA ;

Riera, A .

TETRAHEDRON-ASYMMETRY, 1997, 8 (17) :2967-2974

[2] REACTIVITY OF EPOXIDES .3. METHODS FOR SYNTHESIS OF "1-HYDROXYALKYL-2-VINYLCYCLOPROPANES - REACTION OF GAMMA-DELTA-ETHYLENIC EPOXIDES WITH LITHIUM AMIDES IN HMPT [J].

APPARU, M ;

BARRELLE, M .

TETRAHEDRON, 1978, 34 (11) :1691-1697

[3]

APPARU M, 1976, TETRAHEDRON LETT, V17, P2837

[4] Total syntheses of symbioramide derivatives from L-serine and their antileukemic activities [J].

Azuma, H ;

Takao, R ;

Niiro, H ;

Shikata, K ;

Tamagaki, S ;

Tachibana, T ;

Ogino, K .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (07) :2790-2797

[5] REGIOSELECTIVITY IN CYCLIZATION OF BETA,GAMMA-EPOXY CARBANIONS - APPLICATION TO TOTAL SYNTHESIS OF TRANS-CHRYSANTHEMIC ACID [J].

BABLER, JH ;

TORTORELLO, AJ .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (05) :885-887

[6] METHYL EFFECTS IN THE CYCLIZATION OF GAMMA-EPOXY BIS-SULFONES [J].

BENEDETTI, F ;

BERTI, F ;

FABRISSIN, S ;

GIANFERRARA, T ;

RISALITI, A .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (11) :3530-3537

[7] Kinetic resolution of racemic alkoxy oxiranes by chiral lithium amides [J].

Bigi, A ;

Mordini, A ;

Thurner, A ;

Faigl, F ;

Poli, G ;

Toke, L .

TETRAHEDRON-ASYMMETRY, 1998, 9 (13) :2293-2299

[8] Stability, reactivity, solution, and solid-state structure of halomethylzinc alkoxides [J].

Charette, AB ;

Molinaro, C ;

Brochu, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (49) :12160-12167

[9] The stereoselective cyclopropanation of chiral allylic alcohols using a chiral dioxaborolane ligand:: A new route to anti-cyclopropylmethanol derivatives [J].

Charette, AB ;

Lebel, H ;

Gagnon, A .

TETRAHEDRON, 1999, 55 (29) :8845-8856

[10] CONTROL OF RING SIZE RESULTING FROM GAMMA-EPOXY SULFONE AND GAMMA-EPOXYNITRILE CYCLIZATION - FORMATION OF EITHER CYCLOPROPYL OR CYCLOBUTYL DERIVATIVES [J].

CORBEL, B ;

DURST, T .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (22) :3648-3650

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