Remote Stereoinduction in the Acylation of Fully Substituted Enolates: Tandem Reformatsky/Quaternary Claisen Condensations of Silyl Glyoxylates and β-Lactones

被引：44

作者：

Greszler, Stephen N. ^{[1
]}

Malinowski, Justin T. ^{[1
]}

Johnson, Jeffrey S. ^{[1
]}

机构：

[1] Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 49期

关键词：

COLONY-STIMULATING FACTORS; FAMILY INDUCE PRODUCTION; MARROW STROMAL CELLS; MICROBIAL METABOLITES; ASYMMETRIC-SYNTHESIS; ACID; CONSTRUCTION; ACETALS; SILYLGLYOXYLATES; CYCLOADDITIONS;

D O I：

10.1021/ja108848d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Reformatsky reagents react sequentially with silyl glyoxylates and beta-lactones to give highly functionalized Claisen condensation products. A heretofore undocumented instance of stereochemical 1,4-induction results in efficient transmission of beta-lactone stereochemistry to the emerging fully substituted stereocenter. Second-stage transformations reveal that the five heteroatom-containing functionalities embedded within the products are entirely chemo-differentiated, a circumstance that permits rapid assembly of the leustroducsin B core substructure.

引用

页码：17393 / 17395

页数：3

共 38 条

[1] SOME MOLECULAR-REARRANGEMENTS OF ORGANOSILICON COMPOUNDS [J].

BROOK, AG .

ACCOUNTS OF CHEMICAL RESEARCH, 1974, 7 (03) :77-84

[2] A NOVEL METHOD FOR THE INSITU GENERATION OF ALKOXYDIALKYLBORANES AND THEIR USE IN THE SELECTIVE PREPARATION OF 1,3-SYN DIOLS [J].

CHEN, KM ;

GUNDERSON, KG ;

HARDTMANN, GE ;

PRASAD, K ;

REPIC, O ;

SHAPIRO, MJ .

CHEMISTRY LETTERS, 1987, (10) :1923-1926

[3] DIRECTED REDUCTION OF BETA-HYDROXY KETONES EMPLOYING TETRAMETHYLAMMONIUM TRIACETOXYBOROHYDRIDE [J].

EVANS, DA ;

CHAPMAN, KT ;

CARREIRA, EM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (11) :3560-3578

[4] C2-symmetric Cu(II) complexes as chiral Lewis acids.: Catalytic, enantioselective cycloadditions of silyl ketenes [J].

Evans, DA ;

Janey, JM .

ORGANIC LETTERS, 2001, 3 (13) :2125-2128

[5] ASYMMETRIC ACYLATION REACTIONS OF CHIRAL IMIDE ENOLATES - THE 1ST DIRECT APPROACH TO THE CONSTRUCTION OF CHIRAL BETA-DICARBONYL SYNTHONS [J].

EVANS, DA ;

ENNIS, MD ;

LE, T ;

MANDEL, N ;

MANDEL, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (04) :1154-1156

[6] Total synthesis of theopederin D [J].

Green, Michael E. ;

Rech, Jason C. ;

Floreancig, Paul E. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (38) :7317-7320

[7] Diastereoselective Synthesis of Pentasubstituted γ-Butyrolactones from Silyl Glyoxylates and Ketones through a Double Reformatsky Reaction [J].

Greszler, Stephen N. ;

Johnson, Jeffrey S. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (20) :3689-3691

[8] Catalytic Redox-Initiated Glycolate Aldol Additions of Silyl Glyoxylates [J].

Greszler, Stephen N. ;

Johnson, Jeffrey S. .

ORGANIC LETTERS, 2009, 11 (04) :827-830

[9] Certain condensations brought about by bases. I. The condensation of ethyl isobutyrate to ethyl isobutyryl-isobutyrate [J].

Hauser, CR ;

Renfrow, WB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1937, 59 :1823-1826

[10] NaOH-catalyzed crossed Claisen condensation between ketene silyl acetals and methyl esters [J].

Iida, A ;

Takai, K ;

Okabayashi, T ;

Misaki, T ;

Tanabe, Y .

CHEMICAL COMMUNICATIONS, 2005, (25) :3171-3173

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