Stereoselective transformation of 1-alkeny ether (R 1 CH= CHOMe) into alkene (R 1 CH= CHR 2) based on stereospecific elimination of the vicinal iodo (methoxy) …
A Inoue, K Maeda, H Shinokubo, K Oshima
Index: Inoue, Atsushi; Maeda, Katsuya; Shinokubo, Hiroshi; Oshima, Koichiro Tetrahedron, 1999 , vol. 55, # 3 p. 665 - 674
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Abstract
Treatment of alkenyl methyl ether with ICl rapidly gave 1-chloro-2-iodo-1-methoxyalkane quantitatively. Without isolation, this dihalide was treated with Et3Al to afford anti-iodo (methoxy) alkane in good yield with high stereoselectivity. The stereochemistry of the starting alkenyl ether did not affect the stereochemical outcome of the product. The use of alkynylaluminum ((RC C) 2AlEt) resulted in alkynylation of the α-chloro-β-iodoether. Anti ...
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