Stereoselective C-glycoside formation by a rhodium(I)-catalyzed 1,4-addition of arylboronic acids to acetylated enones derived from glycals

被引：80

作者：

Ramnauth, J ^{[1
]}

Poulin, O ^{[1
]}

Bratovanov, SS ^{[1
]}

Rakhit, S ^{[1
]}

Maddaford, SP ^{[1
]}

机构：

[1] York Univ, MCR Res Inst, Toronto, ON M3J 1P3, Canada

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 16期

关键词：

D O I：

10.1021/ol016245d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A new method for the formation of C-glycosides has been developed employing a cationic rhodium(I)-catalyzed 1,4-addition of arylboronic acids to enones derived from glycals. The reaction is stereoselective for the (x-anomer and is highly dependent on the nature of the rhodium catalyst.

引用

页码：2571 / 2573

页数：3

共 18 条

[1] PALLADIUM-MEDIATED ARYLATION OF ACETYLATED ENONES DERIVED FROM GLYCALS .4. SYNTHESIS OF ARYL 2-DEOXY-BETA-D-C-GLYCOPYRANOSIDES
BENHADDOU, R
CZERNECKI, S
VILLE, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (17) : 4612 - 4616
[2] ASSIGNMENT OF ANOMERIC CONFIGURATION OF C-GLYCOPYRANOSIDES AND C-GLYCOFURANOSIDES - A H-1, C-13, AND NUCLEAR OVERHAUSER ENHANCEMENT SPECTROMETRIC STUDY
BRAKTA, M
FARR, RN
CHAGUIR, B
MASSIOT, G
LAVAUD, C
ANDERSON, WR
SINOU, D
DAVES, GD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (11) : 2992 - 2998
[3] Recent advances in stereoselective C-glycoside synthesis
Du, YG
Linhardt, RJ
Vlahov, IR
[J]. TETRAHEDRON, 1998, 54 (34) : 9913 - 9959
[4] Fürstner A, 2001, ADV SYNTH CATAL, V343, P343
[5] Studies directed toward the total synthesis of scytophycin C: Synthesis of the C(1)-C(18) fragment of scytophycin C
Grieco, PA
Speake, JD
[J]. TETRAHEDRON LETTERS, 1998, 39 (11) : 1275 - 1278
[6] Synthesis of imidazo[1,2-a]pyridine C-nucleosides with an unexpected site of ribosylation
Gudmundsson, KS
Drach, JC
Townsend, LB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (11) : 3453 - 3459
[7] Hacksell U, 1985, Prog Med Chem, V22, P1, DOI 10.1016/S0079-6468(08)70228-5
[8] JARAMILLO C, 1994, SYNTHESIS-STUTTGART, P1
[9] KIRSCHNING A, 1993, SYNLETT, P289
[10] STEREOSPECIFIC SYNTHESIS OF ALPHA-C-ARYL-DELTA(2)-GLYCOPYRANOSIDES AND BETA-C-ARYL-DELTA(2)-GLYCOPYRANOSIDES FROM P-TERT-BUTYLPHENYL ALPHA-O-DELTA(2)-GLYCOPYRANOSIDE VIA GRIGNARD-REAGENTS
MOINEAU, C
BOLITT, V
SINOU, D
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (11) : 1103 - 1104

← 1 2 →