ISSN:
0170-2041
Keywords:
Asymmetric synthesis
;
Diels-Alder reaction
;
Hetero Diels-Alder reaction
;
Aminocyclitols
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The Diels-Alder reaction of cis-5,6-diacetoxy-1,3-cyclohexadiene (1), which has a meso configuration, with the chiral nitroso dienophile 2 occurs with induction of four asymmetric centers in very high optical yield (ee = 94%) and leads to the dihydro oxazine 3 (89%). The influence of the reaction temperature on the asymmetric induction was investigated and the absolute configuration of the product determined. Reductive cleavage of the N — O bond of 3 presents a simple route to enantiomerically pure derivatives of (1R)-conduramine A1 (82%).
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199019900148
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