Nitrone cycloadditions to isolevoglucosenone:: Ready access to a new class of directly linked (1→3)-imino-C-disaccharides

被引：20

作者：

Cardona, F ^{[1
]}

Goti, A ^{[1
]}

Brandi, A ^{[1
]}

机构：

[1] Univ Florence, Dipartimento Chim Organ Ugo Schiff, I-50019 Florence, Italy

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 09期

关键词：

D O I：

10.1021/ol0342507

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

graphic Straightforward access to a new class Of D-gulo- and D-allo-derived directly linked (1-3)-imino-C-disaccharides by means of cycloaddition reactions of enantiopure polyhydroxylated pyrroline N-oxides with isolevoglucosenone is reported. The cycloaddition reactions display a high level of double asymmetric induction, which allows a partial kinetic resolution of a racemic nitrone.

引用

页码：1475 / 1478

页数：4

共 46 条

[1] Aza-C-disaccharides: Synthesis of 6-deoxygalactonojirimycin beta-C(1->3) linked with D-altrofuranosides and D-galactose
Baudat, A
Vogel, P
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (18) : 6252 - 6260
[2] Synthesis of beta-D-(1->3)-C-linked 1,5,6-trideoxy-1,5-iminogalactoside of D-altrose derivatives
Baudat, A
Vogel, P
[J]. TETRAHEDRON LETTERS, 1996, 37 (04) : 483 - 484
[3] REGIO-SELECTIVE AND FACE-SELECTIVE 1,3-DIPOLAR CYCLO-ADDITIONS TO LEVOGLUCOSENONE
BLAKE, AJ
FORSYTH, AC
PATON, RM
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (06) : 440 - 442
[4] 1,3-DIPOLAR CYCLOADDITION REACTIONS OF LEVOGLUCOSENONE
BLAKE, AJ
COOK, TA
FORSYTH, AC
GOULD, RO
PATON, RM
[J]. TETRAHEDRON, 1992, 48 (37) : 8053 - 8064
[5] Cardona F, 1998, SYNLETT, P1444
[6] Cardona F, 2001, EUR J ORG CHEM, V2001, P2999, DOI 10.1002/1099-0690(200108)2001:16<2999::AID-EJOC2999>3.0.CO
[7] 2-4
[8] Cardona F, 1999, EUR J ORG CHEM, V1999, P1319, DOI 10.1002/(SICI)1099-0690(199906)1999:6<1319::AID-EJOC1319>3.0.CO
[9] 2-L
[10] New access to aza-C-disaccharides by cycloadditions of pyrroline N-oxides to glycals
Cardona, F
Valenza, S
Goti, A
Brandi, A
[J]. TETRAHEDRON LETTERS, 1997, 38 (46) : 8097 - 8100

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