Picolinoxy Group, a New Leaving Group for anti SN2′ Selective Allylic Substitution with Aryl Anions Based on Grignard Reagents

The picolinoxy group was found to be an extremely powerful leaving group for allylic substitution with aryl nucleophiles derived from ArMgBr and CuBr•Me2S. The substitution proceeds with anti SN2′ pathway and with high chirality transfer. The electron-withdrawing effect of the pyridyl group and chel...

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Veröffentlicht in:	Organic letters 2008-05, Vol.10 (9), p.1719-1722
Hauptverfasser:	Kiyotsuka, Yohei, Acharya, Hukum P, Katayama, Yuji, Hyodo, Tomonori, Kobayashi, Yuichi
Format:	Artikel
Sprache:	eng
Schlagworte:	Allyl Compounds - chemical synthesis Allyl Compounds - chemistry Anions Indicators and Reagents - chemical synthesis Indicators and Reagents - chemistry Molecular Structure Picolinic Acids - chemistry Piperidines - chemistry Stereoisomerism
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Zusammenfassung:	The picolinoxy group was found to be an extremely powerful leaving group for allylic substitution with aryl nucleophiles derived from ArMgBr and CuBr•Me2S. The substitution proceeds with anti SN2′ pathway and with high chirality transfer. The electron-withdrawing effect of the pyridyl group and chelation to MgBr2 are likely the origin of success. Results suggesting these effects were obtained.
ISSN:	1523-7060 1523-7052
DOI:	10.1021/ol800300x