Development of a new Lewis base-tolerant chiral LBA and its application to catalytic asymmetric protonation reaction

被引：30

作者：

Cheon, Cheol Hong ^{[1
]}

Imahori, Tatsushi ^{[2
]}

Yamamoto, Hisashi ^{[1
]}

机构：

[1] Univ Chicago, Dept Chem, Chicago, IL 60615 USA

[2] Kumamoto Univ, Prior Org Innovat & Excellence, Kumamoto 8608555, Japan

来源：

CHEMICAL COMMUNICATIONS | 2010年 / 46卷 / 37期

关键词：

SILYL ENOL ETHERS; ENANTIOSELECTIVE BIOMIMETIC CYCLIZATION; BRONSTED ACID; TETRACHLORIDE; DITERPENOIDS; POLYPRENOIDS; ACTIVATION; ALCOHOL; ENTRY;

D O I：

10.1039/c0cc02492a

中图分类号：

O6 [化学];

学科分类号：

070301 [无机化学];

摘要：

A new Lewis base-tolerant LBA (Lewis Acid Assisted Bronsted Acid) derived from La(OTf)(3) and (S)-HOP has been developed as a new chiral Bronsted acid. This acid has been successfully applied as a catalyst to asymmetric protonation reactions of silyl enol ethers of 2-substituted cyclic ketones.

引用

收藏

页码：6980 / 6982

页数：3

相关论文

共 29 条

[1]

Stronger bronsted acids [J].

Akiyama, Takahiko .

CHEMICAL REVIEWS, 2007, 107 (12) :5744-5758

[2]

A Bronsted acid catalyst for the enantioselective protonation reaction [J].

Cheon, Cheol Hong ;

Yamamoto, Hisashi .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) :9246-+

[3]

Small-molecule H-bond donors in asymmetric catalysis [J].

Doyle, Abigail G. ;

Jacobsen, Eric N. .

CHEMICAL REVIEWS, 2007, 107 (12) :5713-5743

[4]

Fehr C, 1996, ANGEW CHEM INT EDIT, V35, P2567

[5]

Hydrogen bonding: Single enantiomers from a chiral-alcohol catalyst [J].

Huang, Y ;

Unni, AK ;

Thadani, AN ;

Rawal, VH .

NATURE, 2003, 424 (6945) :146-146

[6]

A new artificial cyclase for polyprenoids:: Enantioselective total synthesis of (-)-chromazonarol, (+)-8-epi-puupehedione, and (-)-11′-deoxytaondiol methyl ether [J].

Ishibashi, H ;

Ishihara, K ;

Yamamoto, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (36) :11122-11123

[7]

Chiral proton donor reagents: Tin tetrachloride-coordinated optically active binaphthol derivatives [J].

Ishibashi, H ;

Ishihara, K ;

Yamamoto, H .

CHEMICAL RECORD, 2002, 2 (03) :177-188

[8]

LEWIS-ACID ASSISTED CHIRAL BRONSTED ACID FOR ENANTIOSELECTIVE PROTONATION OF SILYL ENOL ETHERS AND KETENE BIS(TRIALKYLSILYL) ACETALS [J].

ISHIHARA, K ;

KANEEDA, M ;

YAMAMOTO, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (24) :11179-11180

[9]

The crystallographic structure of a Lewis acid-assisted chiral Bronsted acid as an enantioselective protonation reagent for silyl enol ethers [J].

Ishihara, K ;

Nakashima, D ;

Hiraiwa, Y ;

Yamamoto, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (01) :24-25

[10]

Enantio- and diastereoselective stepwise cyclization of polyprenoids induced by chiral and achiral LBAs. A new entry to (-)-ambrox, (+)-podocarpa-8,11,13-triene diterpenoids, and (-)-tetracyclic polyprenoid of sedimentary origin [J].

Ishihara, K ;

Ishibashi, H ;

Yamamoto, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (14) :3647-3655