𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Benzyne derived from aryloxazolines. A versatile intermediate.

✍ Scribed by A.I. Meyers; William Rieker

Book ID
104220768
Publisher
Elsevier Science
Year
1982
Tongue
French
Weight
175 KB
Volume
23
Category
Article
ISSN
0040-4039

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✦ Synopsis

observed product through a 1,5-H shift (2) or direct proton transfer. A related reaction between benzyne and N-methyl indole derivatives has been reported by Kuehne7 in rather low yields. The ready generation of the oxazoline benzyne 4 and the preliminary success with various nucleophiles leading to 6 (a-e) now opens a route to m-substituted or 1,2,3 substituted benzene derivatives. Further experiments are in progress to extend this methodology to related systems8. ACKNOWLEDGMENT The authors are grateful to the National Institutes of Health support. We thank Dr. Bruce Williams for some early experimental assistance. REFERENCES for financial 1.

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A catalytic asymmetric synthesis of a versatile intermediate for phorbol derivatives
✍ Hideaki Sato; Yun Sik Kim; Masakatsu Shibasaki πŸ“‚ Article πŸ“… 1999 πŸ› Elsevier Science 🌐 French βš– 242 KB

A catalytic asynunetric cyclopropanation of enol silyl ether 9 gave the laetonΒ’ 3 in up to 78% eΒ’. The lactonΒ’ 3 was then Iransformcd into 2, potentially a very versatile intermediate for phorbol analogs, using an inu'amol~cular nitrile oxide cycloaddition as a key step.