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200517.fm Page 42 Friday, March 18, 2005 2:52 PM
2005
Ring closure reactions
O 0130
Domino Reactions that Combine an Azido-Schmidt Ring Expansion with the
Reaction. — Two conceptually different ways concerning the title reac17- 042 Diels—Alder
tion are investigated, 1. an olefinic azide reacts with unsaturated carbonyl compounds,
2. a substrate containing double bonds, azide and keto function reacts with dienes. A
variety of heterocyclic structures is obtained including skeletons of natural products. In
the case of azidoketones (XIV) and cyclohexadiene, only the Diels—Alder adducts
(XX) are observed. — (ZENG, Y.; REDDY, D. S. D.; HIRT, E.; AUBE*, J.; Org. Lett.
6 (2004) 26, 4993-4995; Dep. Med. Chem., Univ. Kans., Lawrence, KS 66045, USA;
Eng.) — Steudel
200517.fm Page 43 Friday, March 18, 2005 2:52 PM
2005
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