Catalytic asymmetric addition of alkylzinc and functionalized alkylzinc reagents to ketones

被引：96

作者：

Jeon, SJ ^{[1
]}

Li, HM ^{[1
]}

García, C ^{[1
]}

LaRochelle, LK ^{[1
]}

Walsh, PJ ^{[1
]}

机构：

[1] Univ Penn, Dept Chem, P Roy & Diana T Vagelos Labs, Philadelphia, PA 19104 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 02期

关键词：

D O I：

10.1021/jo048683e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

DIAGRAM We describe our full report of the catalytic asymmetric addition of simple and functionalized dialkylzinc reagents to a broad range of saturated ketones and enones. The functionalized organozinc reagents contain esters, silyl ethers, alkyl chlorides, and alkyl bromides. In general, the resulting tertiary alcohol products are isolated with high ee's. With some substrates, yields are low as a result of the formation of aldol byproducts. Most substrates undergo additions with good yields reaching as high as 91 %.

引用

页码：448 / 455

页数：8

共 81 条

[41] Catalytic asymmetric addition of diphenylzinc to cyclic α,β-unsaturated ketones [J].

Li, HM ;

García, C ;

Walsh, PJ .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) :5425-5427

[42] Enantioselective alkynylation of aromatic ketones catalyzed by chiral camphorsulfonamide ligands [J].

Lu, G ;

Li, XS ;

Jia, X ;

Chan, WL ;

Chan, ASC .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (41) :5057-5058

[43] Enantioselective addition of AlEt3 to aldehydes catalyzed by titanium(IV)-TADDOLate complex [J].

Lu, JF ;

You, JS ;

Gau, HM .

TETRAHEDRON-ASYMMETRY, 2000, 11 (12) :2531-2535

[44] A catalytic asymmetric method for the synthesis of γ-unsaturated β-amino acid derivatives [J].

Lurain, AE ;

Walsh, PJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (35) :10677-10683

[45] A convenient method for the preparation of inverted tert-alkyl carboxylates from chiral tert-alcohols by a new type of oxidation-reduction, condensation using 2,6-dimethyl-1,4-benzoquinone [J].

Mukaiyama, T ;

Shintou, T ;

Fukumoto, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (35) :10538-10539

[46] ENANTIOSELECTIVE ALKYLATION OF CARBONYL-COMPOUNDS - FROM STOICHIOMETRIC TO CATALYTIC ASYMMETRIC INDUCTION [J].

NOYORI, R ;

SUGA, S ;

KAWAI, K ;

OKADA, S ;

KITAMURA, M .

PURE AND APPLIED CHEMISTRY, 1988, 60 (11) :1597-1606

[47] ASYMMETRIC SYNTHESES BY MEANS OF (-)-SPARTEINE MODIFIED ORGANOMETALLIC REAGENTS [J].

NOZAKI, H ;

ARATANI, T ;

TORAYA, T ;

NOYORI, R .

TETRAHEDRON, 1971, 27 (05) :905-&

[48] ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO BENZALDEHYDE CATALYZED BY A SMALL AMOUNT OF CHIRAL 2-AMINO-1-ALCOHOLS [J].

OGUNI, N ;

OMI, T .

TETRAHEDRON LETTERS, 1984, 25 (26) :2823-2824

[49] ASYMMETRIC AMPLIFYING PHENOMENA IN ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO BENZALDEHYDE [J].

OGUNI, N ;

MATSUDA, Y ;

KANEKO, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (23) :7877-7878

[50] CATALYTIC ASYMMETRIC-SYNTHESIS OF SECONDARY (E)-ALLYL ALCOHOLS FROM ACETYLENES AND ALDEHYDES VIA (1-ALKENYL)ZINC INTERMEDIATES - PRELIMINARY COMMUNICATION [J].

OPPOLZER, W ;

RADINOV, RN .

HELVETICA CHIMICA ACTA, 1992, 75 (01) :170-173

← 1 2 3 4 5 6 7 8 9 →