Highly diastereoselective aldol additions of a chiral ethyl ketone enolate under Lewis base catalysis

被引：18

作者：

Denmark, SE ^{[1
]}

Pham, SM ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 14期

关键词：

D O I：

10.1021/ol0160497

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The aldol addition of a chiral ethyl ketone enolate bearing an oxygen substituent (OTBS) at the alpha -position proceeds with high internal and relative diastereoselectivities with various achiral aldehydes in good yields, The profound influence of the resident stereogenic center allows for the use of an achiral catalyst, such as HMPA, with minor attenuation in internal stereoselectivity,

引用

页码：2201 / 2204

页数：4

共 28 条

[21] STUDIES IN POLYPROPIONATE SYNTHESIS - HIGH PI-FACE SELECTIVITY IN SYN ALDOL REACTIONS OF TIN(II) ENOLATES FROM (R)-1-BENZYLOXY-2-METHYLPENTAN-3-ONE AND (S)-1-BENZYLOXY-2-METHYLPENTAN-3-ONE [J].

PATERSON, I ;

TILLYER, RD .

TETRAHEDRON LETTERS, 1992, 33 (29) :4233-4236

[22] STUDIES IN POLYPROPIONATE SYNTHESIS - HIGH PI-FACE SELECTIVITY IN SYN AND ANTI ALDOL REACTIONS OF CHIRAL BORON ENOLATES OF LACTATE-DERIVED KETONES [J].

PATERSON, I ;

WALLACE, DJ ;

VELAZQUEZ, SM .

TETRAHEDRON LETTERS, 1994, 35 (48) :9083-9086

[23] MANIPULATION OF THE ALDOL ADDUCTS FROM LACTATE-DERIVED KETONES - A VERSATILE CHIRAL AUXILIARY FOR THE ASYMMETRIC-SYNTHESIS OF BETA-HYDROXY CARBONYL-COMPOUNDS [J].

PATERSON, I ;

WALLACE, DJ .

TETRAHEDRON LETTERS, 1994, 35 (48) :9087-9090

[24]

PATERSON I, 2000, MODERN CARBONYL CHEM, pCH9

[25] STRUCTURAL, MECHANISTIC, AND THEORETICAL ASPECTS OF CHELATION-CONTROLLED CARBONYL ADDITION-REACTIONS [J].

REETZ, MT .

ACCOUNTS OF CHEMICAL RESEARCH, 1993, 26 (09) :462-468

[26] ON 1,4-DIASTEREOSELECTIVITY IN THE ALDOL CONDENSATION OF METHYL KETONES [J].

TROST, BM ;

URABE, H .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (13) :3982-3983

[27] NUCLEOSIDE SYNTHESES .22. NUCLEOSIDE SYNTHESIS WITH TRIMETHYLSILYL TRIFLATE AND PERCHLORATE AS CATALYSTS [J].

VORBRUGGEN, H ;

KROLIKIEWICZ, K ;

BENNUA, B .

CHEMISCHE BERICHTE-RECUEIL, 1981, 114 (04) :1234-1255

[28] THEXYLDIMETHYLSILYL CHLORIDE, AN EASILY ACCESSIBLE REAGENT FOR THE PROTECTION OF ALCOHOLS [J].

WETTER, H ;

OERTLE, K .

TETRAHEDRON LETTERS, 1985, 26 (45) :5515-5518

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