𝔖 Bobbio Scriptorium
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Ring expansion by in situ tethering of hydroxy azides to ketones: The boyer reaction

✍ Scribed by Vijaya Gracias; Kristine E. Frank; Gregory L. Milligan; Jeffrey Aubé

Book ID
104208124
Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
798 KB
Volume
53
Category
Article
ISSN
0040-4020

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✦ Synopsis

Although alkyl azides can react with ketones to torm ring-expanded lactams, the reaction suffers from poor generality and the need to use powerful Lewis acid promotion. The reactions of 1,2-and 1,3-hydroxyalkyl azides with ketones yield N-hydroxyalkyl lactams in high yields under the action of protic or Lewis acids such as BF3oOEt2 . The reaction appears to succeed due to the initial formation of a hemiketal, which then renders the attack of azide on an oxonium ion intramolecular. The scope of this reaction vis ' ~ vis ketone and hydroxyalkyl azide structure is discussed.

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✍ Yumi Yahiro; Satoshi Ichikawa; Satoshi Shuto; Akira Matsuda 📂 Article 📅 1999 🏛 Elsevier Science 🌐 French ⚖ 288 KB

A stereoselective method for introducing a C2-unit at the 1 or-and 1 I~-postions of D-glucose and D-mannose, respectively, via a radical cyclization reaction with vinylsilyl group as a temporary connecting tether, was developed. The radical cyclization of D-glucose substrates was effectively facilit