Annulations of Enantioenriched Allenylsilanes with in Situ Generated Iminium Ions: Stereoselective Synthesis of Diverse Heterocycles

被引：30

作者：

Brawn, Ryan A.

Panek, James S. ^{[1
]}

机构：

[1] Boston Univ, Dept Chem, Boston, MA 02215 USA

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 02期

关键词：

ASYMMETRIC-SYNTHESIS; FUNCTIONALIZED PYRROLIDINES; ALLENES; CYCLIZATION; 3-COMPONENT; DERIVATIVES; ALDEHYDES; ESTER;

D O I：

10.1021/ol802618p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly enantioenriched allenylsilanes; participate in Lewis acid mediated annulations with in situ generated iminium ions derived from tertbutyl carbamate and methyl carbamate to selectively form functionalized 4,5-dihydropyrroles and 4,5-dihyrooxazines, respectively. The dihydropyrrole products were further elaborated in a stereocontrolled vinylsilane terminated cyclization with in situ generated oxonium ions, resulting in pyranopyrroles.

引用

收藏

页码：473 / 476

页数：4

相关论文

共 19 条

[1] VINYLSILANE-TERMINATED AND ALKYNYLSILANE-TERMINATED CYCLIZATION REACTIONS [J].

BLUMENKOPF, TA ;

OVERMAN, LE .

CHEMICAL REVIEWS, 1986, 86 (05) :857-873

[2] Preparation and use of enantioenriched allenylsilanes for the stereoselective synthesis of homopropargylic ethers [J].

Brawn, Ryan A. ;

Panek, James S. .

ORGANIC LETTERS, 2007, 9 (14) :2689-2692

[3] Small-molecule inhibitors of protein geranylgeranyltransferase type I [J].

Castellano, Sabrina ;

Fiji, Hannah D. G. ;

Kinderman, Sape S. ;

Watanabe, Masaru ;

de Leon, Pablo ;

Tamanoi, Fuyuhiko ;

Kwon, Ohyun .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (18) :5843-+

[4] Cu(I)-catalyzed enantioselective [3+2] cycloaddition reaction of 1-alkylallenylsilane with α-imino ester:: Asymmetric synthesis of dehydroproline derivatives [J].

Daidouji, K ;

Fuchibe, K ;

Akiyama, T .

ORGANIC LETTERS, 2005, 7 (06) :1051-1053

[5] APPLICATION OF ALLENYLSILANES IN [3 + 2] ANNULATION APPROACHES TO OXYGEN AND NITROGEN-HETEROCYCLES [J].

DANHEISER, RL ;

KWASIGROCH, CA ;

TSAI, YM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (24) :7233-7235

[6] SCOPE AND STEREOCHEMICAL COURSE OF THE ADDITION OF (TRIMETHYLSILYL)ALLENES TO KETONES AND ALDEHYDES - A REGIOCONTROLLED SYNTHESIS OF HOMOPROPARGYLIC ALCOHOLS [J].

DANHEISER, RL ;

CARINI, DJ ;

KWASIGROCH, CA .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (20) :3870-3878

[7] A NEW SYNTHESIS OF SUBSTITUTED FURANS [J].

DANHEISER, RL ;

STONER, EJ ;

KOYAMA, H ;

YAMASHITA, DS ;

KLADE, CA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (12) :4407-4413

[8]

Depature M, 2001, EUR J ORG CHEM, V2001, P941

[9] Cooperative, highly enantioselective phosphinothiourea catalysis of imine-allene [3+2] cycloadditions [J].

Fang, Yuan-Qing ;

Jacobsen, Eric N. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (17) :5660-+

[10] Enantioselective three-component synthesis of 4-arylated dehydroprolines:: [3+2] annulation of allenylstannane and α-imino ester [J].

Fuchibe, K ;

Hatemata, R ;

Akiyama, T .

TETRAHEDRON LETTERS, 2005, 46 (49) :8563-8566