Highly diastereo- and enantioselective reagents for aldehyde crotylation

被引：85

作者：

Hackman, BM ^{[1
]}

Lombardi, PJ ^{[1
]}

Leighton, JL ^{[1
]}

机构：

[1] Columbia Univ, Dept Chem, New York, NY 10027 USA

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 23期

关键词：

D O I：

10.1021/ol0480731

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two new, crystalline solid, storable, and highly enantioselective reagents for aldehyde crotylation have been developed. Both (cis and trans) crotylsilane reagents are easily prepared in bulk, require trivial reaction conditions, and provide the homoallylic alcohol products with near diastereo- and enantiospecificity in many cases.

引用

收藏

页码：4375 / 4377

页数：3

相关论文

共 16 条

[1]

[Anonymous], MODERN CARBONYL CHEM

[2] Enantioselective allylation of ketone-derived benzoylhydrazones: Practical synthesis of tertiary carbinarnines [J].

Berger, R ;

Duff, K ;

Leighton, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (18) :5686-5687

[3] Toward a versatile allylation reagent: Practical, enantioselective allylation of acylhydrazones using strained silacycles [J].

Berger, R ;

Rabbat, PMA ;

Leighton, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (32) :9596-9597

[4] CHIRAL SYNTHESIS VIA ORGANOBORANES .21. ALLYLBORATION AND CROTYLBORATION OF ALPHA-CHIRAL ALDEHYDES WITH DIISOPINOCAMPHEYLBORON AS THE CHIRAL AUXILIARY [J].

BROWN, HC ;

BHAT, KS ;

RANDAD, RS .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (07) :1570-1576

[5]

Denmark S. E., 2000, MODERN CARBONYL CHEM

[6] Catalytic, enantioselective addition of substituted allylic trichlorosilanes using a rationally-designed 2,2′-bispyrrolidine-based bisphosphoramide [J].

Denmark, SE ;

Fu, JP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (38) :9488-9489

[7] ON THE STEREOCHEMISTRY OF ALLYLMETAL-ALDEHYDE CONDENSATIONS [J].

DENMARK, SE ;

WEBER, EJ .

HELVETICA CHIMICA ACTA, 1983, 66 (06) :1655-1660

[8] ENANTIOSELECTIVE ALLYLTITANATION OF ALDEHYDES WITH CYCLOPENTADIENYLDIALKOXYALLYLTITANIUM COMPLEXES [J].

HAFNER, A ;

DUTHALER, RO ;

MARTI, R ;

RIHS, G ;

ROTHESTREIT, P ;

SCHWARZENBACH, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (07) :2321-2336

[9] Asymmetric allylation of aromatic aldehydes catalyzed by chiral phosphoramides prepared from (S)-proline [J].

Iseki, K ;

Kuroki, Y ;

Takahashi, M ;

Kishimoto, S ;

Kobayashi, Y .

TETRAHEDRON, 1997, 53 (10) :3513-3526

[10] Strained silacycles in organic synthesis: A new reagent for the enantioselective allylation of aldehydes [J].

Kinnaird, JWA ;

Ng, PY ;

Kubota, K ;

Wang, XL ;

Leighton, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (27) :7920-7921