First asymmetric hetero Diels-Alder reaction of 1-sulfinyl dienes with nitroso derivatives.: A new entry to the synthesis of optically pure 1,4-imino-1-ribitol derivatives

被引：38

作者：

Arribas, C

Carreño, MC ^{[1
]}

García-Ruano, JL

Rodríguez, JF

Santos, M

Sanz-Tejedor, MA

机构：

[1] Univ Autonoma Madrid, Dept Quim Organ C 1, E-28049 Madrid, Spain

[2] Univ Valladolid, Dept Quim Organ, ETSII, E-47011 Valladolid, Spain

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 20期

关键词：

D O I：

10.1021/ol0063611

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Hetero Diels-Alder (HDA) cycloaddition of chiral 1-p-tolylsulfinyl-1,3-pentadiene with benzyl nitrosoformate, under mild conditions, yields 2H-1,2-oxazine 3 with complete regioselectivity and pi-facial diastereoselectivity. Sequential osmylation and protection of the resulting glycol gives the oxazine 5 which is directly transformed into enantiomerically pure 1,4,5 trideoxy-1,4-imino L-ribitol 8 by reduction under Pd/C.

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页码：3165 / 3168

页数：4

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