Halohydroxylation of alkylidenecyclopropanes using N-halosuccinimide (NXS) as the halogen source: an efficient synthesis of halocyclopropylmethanol and 3-halobut-3-en-1-ol derivatives

被引：21

作者：

Yang, Yewei ^{[1
]}

Su, Chenliang ^{[1
]}

Huang, Xian ^{[1
,2
]}

Liu, QingYang ^{[1
]}

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310028, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 41期

基金：

中国国家自然科学基金;

关键词：

METHYLENECYCLOPROPANES; ALDEHYDES; SULFONES; SELENOSULFONATION; HYDROZIRCONATION; HYDROAMINATION; ALKENES; OLEFINS; KETONES;

D O I：

10.1016/j.tetlet.2009.07.146

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of halocyclopropyl-methanol and 3-halo-but-3-en-1-ol derivatives were prepared in moderate to excellent yields via the simple halohydroxylation reaction of alkylidenecyclopropanes with convenient and mild sources of electrophilic halogen NXS (X = I, Br, Cl, F) and H2O. A plausible mechanism for the halohydroxylation has been proposed. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：5754 / 5756

页数：3

共 50 条

[1] SELENOSULFONATION OF ACETYLENES - SUBSTITUTION-REACTIONS OF BETA-(PHENYLSELENO)VINYL SULFONES WITH ORGANOCUPRATES [J].

BACK, TG ;

COLLINS, S ;

LAW, KW .

TETRAHEDRON LETTERS, 1984, 25 (16) :1689-1692

[2] PREPARATION OF ALLENIC SULFONES AND ALLENES FROM THE SELENOSULFONATION OF ACETYLENES [J].

BACK, TG ;

KRISHNA, MV ;

MURALIDHARAN, KR .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (17) :4146-4153

[3] Copper-catalyzed synthesis of 1,3-enynes [J].

Bates, CG ;

Saejueng, P ;

Venkataraman, D .

ORGANIC LETTERS, 2004, 6 (09) :1441-1444

[4] Synthesis of mono-, di-, and trisilyl-substituted alkenes via the hydrosilylation of methylenecyclopropanes catalyzed by Rh(I) complexes [J].

Bessmertnykh, AG ;

Blinov, KA ;

Grishin, YK ;

Donskaya, NA ;

Tveritinova, EV ;

Yureva, NM ;

Beletskaya, IP .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (17) :6069-6076

[5] Synthesis of methylene- and alkylidenecyclopropane derivatives [J].

Brandi, A ;

Goti, A .

CHEMICAL REVIEWS, 1998, 98 (02) :589-635

[6] Heterocycles from alkylidenecyclopropanes [J].

Brandi, A ;

Cicchi, S ;

Cordero, FM ;

Goti, A .

CHEMICAL REVIEWS, 2003, 103 (04) :1213-1269

[7] REACTIONS OF 1-BROMO-1-LITHIOCYCLOPROPANES WITH KETONES AND ALDEHYDES - NEW METHOD OF CONVERTING OLEFINS INTO OXASPIROPENTANES, CYCLOBUTANONES, CYCLOPROPYL KETONES, AND LACTONES [J].

BRAUN, M ;

DAMMANN, R ;

SEEBACH, D .

CHEMISCHE BERICHTE-RECUEIL, 1975, 108 (07) :2368-2390

[8] Expeditious formal synthesis of (±)-epibatidine using diastereoselective bromohydroxylation of aminocyclohexene derivatives [J].

Cabanal-Duvillard, I ;

Berrien, JF ;

Royer, J ;

Husson, HP .

TETRAHEDRON LETTERS, 1998, 39 (29) :5181-5184

[9] Palladium-catalyzed addition of alcohol pronucleophiles to alkylidenecyclopropanes [J].

Camacho, DH ;

Nakamura, I ;

Saito, S ;

Yamamoto, Y .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (01) :270-275

[10] Probing the SAR of dEpoB via chemical synthesis: A total synthesis evaluation of C26-(1,3-dioxolanyl)-12,13-desoxyepothilone B [J].

Chappell, MD ;

Harris, CR ;

Kuduk, SD ;

Balog, A ;

Wu, Z ;

Zhang, F ;

Lee, CB ;

Stachel, SJ ;

Danishefsky, SJ ;

Chou, TC ;

Guan, Y .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (22) :7730-7736

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