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Facile Hetero-Diels-Alder Reaction of α,β-Unsaturated Acyl Cyanides and Enol Ethers: Syntheses of 2-Alkoxy-3,4-dihydro-2H-Pyran-6-carbonitriles

✍ Scribed by Robert A. John; Vincent Schmid; Hugo Wyler

Publisher: John Wiley and Sons
Year: 1987
Tongue: German
Weight: 487 KB
Volume: 70
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19870700313

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✦ Synopsis

2-Ethoxy-3,4-dihydro-2H-pyran-6-carbonitriles are obtained in high yield by stereospecific endo-mode cycloadditions of ccJ-unsaturated acyl cyanides and ethyl vinyl cther at room temperature. The nitrile group is converted to some other functionalities.

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## Abstract Cycloadditions of the α,β‐unsaturated‐acyl cyanides 1–3 with (__Z__)‐or (__E__)‐1‐bromo‐2‐ethoxyethene (4) may be performed at moderate temperatures and provide in good yields the 3‐bromo‐2‐ethoxy‐3,4‐dihydro‐2__H__‐pyran‐6‐carbonitriles 5–7, respectively (__Scheme 1__). Diastereoisomer

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