Thermal induced intramolecular [2+2] cycloaddition of allene-ACPs

被引：32

作者：

Chen, Kai ^{[1
,2
]}

Sun, Run ^{[1
,2
]}

Xu, Qin ^{[1
,2
]}

Wei, Yin ^{[3
]}

Shi, Min ^{[1
,2
,3
]}

机构：

[1] E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China

[2] E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China

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

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2013年 / 11卷 / 24期

基金：

中国国家自然科学基金;

关键词：

UNIQUE TETRASUBSTITUTED ALKENE; MGI2-MEDIATED RING EXPANSIONS; ACID-MEDIATED CYCLOADDITION; TETHERED ALKYLIDENECYCLOPROPANES; CYCLOBUTANE DERIVATIVES; PYRROLIDINE SKELETONS; BOND-CLEAVAGE; METHYLENECYCLOPROPANES; EFFICIENT; LEWIS;

D O I：

10.1039/c3ob40911b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile synthetic method for preparation of bicyclo[4.2.0] nitrogen heterocycles has been developed via a thermal induced intramolecular [2 + 2] cycloaddition reaction of allene-ACPs. The DFT calculations indicate that this intramolecular cycloaddition proceeds in a concerted manner and a strained small ring is essential.

引用

页码：3949 / 3953

页数：5

共 69 条

[61] Enantioselective catalytic ring expansion of methylenecyclopropane carboxamides promoted by a chiral magnesium Lewis acid [J].

Taillier, Catherine ;

Lautens, Mark .

ORGANIC LETTERS, 2007, 9 (04) :591-593

[62] HOTf-Catalyzed Rearrangement of Methylenecyclopropane Aryl and Alkyl Alcohols [J].

Tang, Xiang-Ying ;

Shi, Min .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (21) :4106-4110

[63] Gold(I)-catalyzed additions of three-component 2-(arylmethylene)cyclopropylcarbinols, terminal arynes, and alcohols: An efficient access to 3-oxabicyclo[3.1.0]hexanes [J].

Tian, Guo-Qiang ;

Shi, Min .

ORGANIC LETTERS, 2007, 9 (23) :4917-4920

[64] THE ATOM ECONOMY - A SEARCH FOR SYNTHETIC EFFICIENCY [J].

TROST, BM .

SCIENCE, 1991, 254 (5037) :1471-1477

[65] On inventing reactions for atom economy [J].

Trost, BM .

ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (09) :695-705

[66] Ring opening in the palladium-catalyzed hydrocarbonation of methylenecyclopropanes with pronucleophiles [J].

Tsukada, N ;

Shibuya, A ;

Nakamura, I ;

Yamamoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (34) :8123-8124

[67] Recent Advances on the Preparation and Reactivity of Methylenecyclopropanes [J].

Yu, Lei ;

Guo, Rong .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2011, 43 (02) :209-259

[68] Gold(I)-Catalyzed Cycloisomerization of Nitrogen- and Oxygen-Tethered Alkylidenecyclopropanes to Tricyclic Compounds [J].

Zhang, Di-Han ;

Wei, Yin ;

Shi, Min .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (23) :7026-7029

[69] Titanium(IV) chloride-mediated intramolecular ring enlargement of methylenecyclopropanes with propargylic esters: a concise synthesis of bicyclo[4.2.0]oct-5-ene derivatives [J].

Zhang, Zhen ;

Shi, Min .

TETRAHEDRON LETTERS, 2011, 52 (49) :6541-6544

← 1 2 3 4 5 6 7 →