Rhodium-catalyzed enantio- and diastereoselective intramolecular [2+2+2] cycloaddition of unsymmetrical dienynes

被引：30

作者：

Sagae, Hiromi ^{[1
]}

Noguchi, Keiichi ^{[2
]}

Hirano, Masao ^{[1
]}

Tanaka, Ken ^{[1
]}

机构：

[1] Tokyo Univ Agr & Technol, Grad Sch Engn, Dept Appl Chem, Koganei, Tokyo 1848588, Japan

[2] Tokyo Univ Agr & Technol, Instrumentat Anal Ctr, Koganei, Tokyo 1848588, Japan

来源：

CHEMICAL COMMUNICATIONS | 2008年 / 32期

关键词：

D O I：

10.1039/b804294b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A cationic rhodium(I)/(R)-H-8-BINAP or (R)-Segphos complex catalyzes an intramolecular 12 + 2 + 21 cycloaddition of unsymmetrical dienynes, leading to fused tri- and tetracyclic cyclohexenes bearing two tertiary or quaternary carbon centers in high yields with high enantio- and diastereoselectivity.

引用

页码：3804 / 3806

页数：3

共 24 条

[11] Enantioselective construction of quaternary carbon centers by catalytic [2+2+2] cycloaddition of 1,6-enynes and alkynes [J].

Shibata, T ;

Arai, Y ;

Tahara, Y .

ORGANIC LETTERS, 2005, 7 (22) :4955-4957

[12] Rhodium-catalyzed enantioselective [2+2+2] cycloaddition of diynes with unfunctionalized alkenes [J].

Shibata, Takanori ;

Kawachi, Ai ;

Ogawa, Mika ;

Kuwata, Yusuke ;

Tsuchikarna, Kyoji ;

Endo, Kohei .

TETRAHEDRON, 2007, 63 (52) :12853-12859

[13] Enantioselective intramolecular [2+2+2] cycloaddition of enediynes for the synthesis of chiral cyclohexa-1,3-dienes [J].

Shibata, Takanori ;

Kurokawa, Hiroshi ;

Kanda, Kazumasa .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (17) :6521-6525

[14] Enantioselective intramolecular [2+2+2] cycloaddition of 1,4-diene-ynes: A new approach to the construction of quaternary carbon stereocenters [J].

Shibata, Takanori ;

Tahara, Yu-ki .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (36) :11766-11767

[15] Transition metal catalysed synthesis of tetrahydro derivatives of [5]-, [6]- and [7]helicene [J].

Stará, IG ;

Stary, I ;

Kollárovic, A ;

Teply, F ;

Vyskocil, S ;

Saman, D .

TETRAHEDRON LETTERS, 1999, 40 (10) :1993-1996

[16] Ruthenium-Catalyzed [2+2+2] Cocyclization of Diene-yne [J].

Tanaka, Daisuke ;

Sato, Yoshihiro ;

Mori, Miwako .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (25) :7730-+

[17] Highly chemo- and regioselective intermolecular cyclotrimerization of alkynes catalyzed by cationic rhodium(I)/modified BINAP [J].

Tanaka, K ;

Shirasaka, K .

ORGANIC LETTERS, 2003, 5 (24) :4697-4699

[18] Enantioselective synthesis of planar-chiral metacyclophanes through cationic Rh(I)/modified-BINAP-catalyzed inter- and intramolecular alkyne cyclotrimerizations [J].

Tanaka, Ken ;

Sagae, Hirorni ;

Toyoda, Kazuki ;

Hirano, Masao .

TETRAHEDRON, 2008, 64 (05) :831-846

[19] Enantioselective synthesis of C2-symmetric dimethyl cyclohexadiene-dicarboxylates through cationic rhodium(I)/modified-BINAP-catalyzed [2+2+2] cycloadditions [J].

Tanaka, Ken ;

Nishida, Goushi ;

Sagae, Hiromi ;

Hirano, Masao .

SYNLETT, 2007, (09) :1426-1430

[20] Development of chemo-, regio-, and enantioselective [2+2+2] cycloadditions catalyzed by cationic Rhodium(I)/BINAP-type bisphosphine complexes [J].

Tanaka, Ken ;

Nishida, Goushi ;

Suda, Takeshi .

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2007, 65 (09) :862-873

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