Synthesis of α-Keto-Imides via Oxidation of Ynamides

被引：84

作者：

Al-Rashid, Ziyad F. ^{[1
,2
]}

Johnson, Whitney L. ^{[1
,2
]}

Hsung, Richard P. ^{[1
,2
]}

Wei, Yonggang ^{[1
,2
]}

Yao, Pei-Yuan ^{[3
]}

Liu, Renhei ^{[3
]}

Zhao, Kang ^{[3
]}

机构：

[1] Univ Wisconsin, Div Pharmaceut Sci, Madison, WI 53705 USA

[2] Univ Wisconsin, Dept Chem, Madison, WI 53705 USA

[3] Tianjin Univ, Coll Pharmaceut & Biotechnol, Tianjin 300072, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 22期

关键词：

D O I：

10.1021/jo8015067

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A de novo preparation of alpha-keto-imides via ynamide oxidation is described. With a number of alkyne oxidation conditions screened, a highly efficient RuO2-NaIO4 mediated oxidation and a DMDO oxidation have been identified to tolerate a wide range of ynamide types. In addition to accessing a wide variety of a-keto-imides, the RuO2-NaIO4 protocol provides a novel entry to the vicinal tricarboryl motif via oxidation of push-pull ynamides, and imido acylsilanes from silyl-substituted ynamides. Chemoselective oxidation of ynamides containing olefins can be achieved by using DMDO, while the RuO2-NaIO4 protocol is not effective. These studies provide further support for the synthetic utility of ynamides.

引用

页码：8780 / 8784

页数：5

共 78 条

[1] Reactive intermediates from DMDO oxidation of ynamides. Trapping of a de novo chiral push-pull carbene via cyclopropanation [J].

Al-Rashid, Ziyad F. ;

Hsung, Richard P. .

ORGANIC LETTERS, 2008, 10 (04) :661-663

[2] ALPHA-DIKETONE AND ALPHA-KETO ESTER DERIVATIVES OF N-PROTECTED AMINO-ACIDS AND PEPTIDES AS NOVEL INHIBITORS OF CYSTEINE AND SERINE PROTEINASES [J].

ANGELASTRO, MR ;

MEHDI, S ;

BURKHART, JP ;

PEET, NP ;

BEY, P .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (01) :11-13

[3] NOVEL APPLICATIONS OF POTASSIUM CHLORATE OSMIUM TETROXIDE OXIDIZING SYSTEM - SYNTHESIS OF ALPHA-DICARBONYL DERIVATIVES FROM ACETYLENIC-COMPOUNDS - SYNTHESIS OF A 2,3-DIHYDROXY-1,4-DIONE FROM A 2,5-DIALKYLFURAN [J].

BASSIGNANI, L ;

BRANDT, A ;

CACIAGLI, V ;

RE, L .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (21) :4245-4247

[4] Synthesis and use of α-silyl-substituted α-hydroxyacetic acids [J].

Bolm, C ;

Kasyan, A ;

Heider, P ;

Saladin, S ;

Drauz, K ;

Günther, K ;

Wagner, C .

ORGANIC LETTERS, 2002, 4 (13) :2265-2267

[5] A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS [J].

CARLSEN, PHJ ;

KATSUKI, T ;

MARTIN, VS ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3936-3938

[6] Diastereoselective allylation of α-ketoamides bearing camphor N-tosylpyrazolidinone auxiliary:: Efficient synthesis of highly optically active two stereoisomers [J].

Chen, JH ;

Venkatesham, U ;

Lee, LC ;

Chen, KM .

TETRAHEDRON, 2006, 62 (05) :887-893

[7] Rapid synthesis of α-ketoamides using microwave irradiation-simultaneous cooling method [J].

Chen, JJ ;

Deshpande, SV .

TETRAHEDRON LETTERS, 2003, 44 (49) :8873-8876

[8] Synthesis of α-ketoamides from a carbamoylsilane and acid chlorides [J].

Chen, JX ;

Cunico, RF .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (16) :5509-5511

[9] Synthesis and study of a lipophilic α-keto amide inhibitor of pancreatic lipase [J].

Chiou, A ;

Markidis, T ;

Constantinou-Kokotou, V ;

Verger, R ;

Kokotos, G .

ORGANIC LETTERS, 2000, 2 (03) :347-350

[10] STUDIES ON ASYMMETRIC SYNTHESIS OF ALPHA-AMINO ACIDS .1. A NEW APPROACH [J].

COREY, EJ ;

MCCAULLY, RJ ;

SACHDEV, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (08) :2476-+

← 1 2 3 4 5 6 7 8 →