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Remarkable O 2 -Effect in 1,4-Additions of Diethylzinc to 6-Acyloxy-2 H -pyran-3(6 H )-ones and 6-Alkoxy-2 H -pyran-3(6 H )-ones

✍ Scribed by van der Deen, Hanneke; Kellogg, Richard M.; Feringa, Ben L.

Book ID
126974628
Publisher
American Chemical Society
Year
2000
Tongue
English
Weight
72 KB
Volume
2
Category
Article
ISSN
1523-7060

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## Abstract The 6‐hydroxy‐2H‐pyran‐3(6H)‐ones 1a–d are esterified stereoselectively with acetic and formic acid, and with several amino acids and peptide derivatives using the DCC/DMAP method. The direct synthesis of the 6‐alkoxy derivatives 3g–k is also studied.

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## 2 , : 'H-NMR (CDCI,): 5.93 (dd, J = 10.7. 1.5); 5.67 6a. 7.7,8,octun-S-oiir @a): 'H-NMR (CDCI,): 3.98, 3.78 ( A R , . 0 ] o l l a l r (9a): ' H-N MR (CDCI,) : 4.02, 3.65 (.4 R, -c/io.~-aspiro~3.5/nori-X-i~.nr~ (7b): 'H-NMR (CDCI,): 6.04 (d, J = 10.4); 5.63 (d, ( d , J = 10.7);4.I0(dd,J=11.7,1.