Catalytic Asymmetric Conjugate Addition of α-Cyanoketones for the Construction of a Quaternary Stereogenic Center

被引：35

作者：

Kawato, Yuji ^{[1
]}

Takahashi, Noriko ^{[1
]}

Kumagai, Naoya ^{[1
]}

Shibasaki, Masakatsu ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 07期

关键词：

DIELS-ALDER REACTIONS; ENANTIOSELECTIVE CONSTRUCTION; MICHAEL ADDITIONS; ALPHA; BETA-UNSATURATED KETONES; 1,3-DICARBONYL COMPOUNDS; SYNTHETIC ENZYMES; ALDOL REACTIONS; STEREOCENTERS; EPOXIDATION; CYANOACETATES;

D O I：

10.1021/ol100183s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The catalytic asymmetric conjugate addition of alpha-cyanoketone pronucleophiles to vinyl ketones promoted by a Y/1 catalyst is described. High enantioselectivity was observed for a range of aromatic vinyl ketones, providing 1,5-dicarbonyl compounds bearing an all-carbon quaternary stereogenic center. The product was successfully converted to a spiro-piperidine entity and a bicyclo[3.3.0]octane framework through either the reduction of nitrile or intramolecular pinacol coupling.

引用

页码：1484 / 1487

页数：4

共 66 条

[21] Use of samarium diiodide in the field of asymmetric synthesis [J].

Gopalaiah, Kovuru ;

Kagan, Henri B. .

NEW JOURNAL OF CHEMISTRY, 2008, 32 (04) :607-637

[22] Catalytic asymmetric aldol reactions in aqueous media using chiral bis-pyridino-18-crown-6-rare earth metal triflate complexes [J].

Hamada, T ;

Manabe, K ;

Ishikawa, S ;

Nagayama, S ;

Shiro, M ;

Kobayashi, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (10) :2989-2996

[23] Direct generation of nucleophilic chiral palladium enolate from 1,3-dicarbonyl compounds: Catalytic enantioselective Michael reaction with enones [J].

Hamashima, Y ;

Hotta, D ;

Sodeoka, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (38) :11240-11241

[24] Small peptides as ligands for catalytic asymmetric alkylations of olefins. Rational design of catalysts or of searches that lead to them? [J].

Hoveyda, AH ;

Hird, AW ;

Kacprzynski, MA .

CHEMICAL COMMUNICATIONS, 2004, (16) :1779-1785

[25] POLYMER-SUPPORTED POLY(AMINO ACIDS) AS NEW ASYMMETRIC EPOXIDATION CATALYST OF ALPHA,BETA-UNSATURATED KETONES [J].

ITSUNO, S ;

SAKAKURA, M ;

ITO, K .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (24) :6047-6049

[26] RETRACTED: Asymmetric catalysis of the Strecker amino acid synthesis by a cyclic dipeptide (Retracted article. See JUN, 2023) [J].

Iyer, MS ;

Gigstad, KM ;

Namdev, ND ;

Lipton, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (20) :4910-4911

[27] Catalytic Asymmetric Michael Additions of α-Cyanoacetates [J].

Jautze, Sascha ;

Peters, Rene .

SYNTHESIS-STUTTGART, 2010, (03) :365-388

[28] "Synthetic Enzymes". Highly Stereoselective Epoxidation of Chalcone in a Triphasic Toluene-Water-Poly[(S)-alanine] System [J].

Julia, S. ;

Vega, J. C. .

AFINIDAD, 2024, 81 (603) :929-931

[29]

Kanai M., 2000, CATALYTIC ASYMMETRIC, V2nd, P569

[30] Oligopeptides as catalysts for asymmetric epoxidation [J].

Kelly, DR ;

Roberts, SM .

BIOPOLYMERS, 2006, 84 (01) :74-89

← 1 2 3 4 5 6 7 →