TY - JOUR
T1 - Reductive Generation of Aldehyde Metal Enolate from Ketene. A One-Flask Process to 1,1,2-and 1,2,2-Trisubstituted Dihydronaphthalenes from 1- and 2-Naphthalenecarboxylates
AU - Tomioka, Kiyoshi
AU - Shindo, Mitsuru
AU - Koga, Kenji
PY - 1990
Y1 - 1990
N2 - Successive treatment of 2,6-di-fert-buty1-4-(methoxypheny1)-1- and -2-naphthalenecarboxylates (BHAesters) (1, 2) with organolithium in THE, lithium triethylborohydride in refluxing THE, methyl iodide-HMPA, and finally sodium borohydride in MeOH provided regioand stereoselectively 1,1,2- and 1,2,2-trisubstituted dihydronaphthalenes (3, 4), respectively, in good yields. This one-flask process is constituted from a sequence of five reactions involving reductive generation of aldehyde metal enolate from ketene as a key step.
AB - Successive treatment of 2,6-di-fert-buty1-4-(methoxypheny1)-1- and -2-naphthalenecarboxylates (BHAesters) (1, 2) with organolithium in THE, lithium triethylborohydride in refluxing THE, methyl iodide-HMPA, and finally sodium borohydride in MeOH provided regioand stereoselectively 1,1,2- and 1,2,2-trisubstituted dihydronaphthalenes (3, 4), respectively, in good yields. This one-flask process is constituted from a sequence of five reactions involving reductive generation of aldehyde metal enolate from ketene as a key step.
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U2 - 10.1021/jo00295a005
DO - 10.1021/jo00295a005
M3 - Article
AN - SCOPUS:0001125312
SN - 0022-3263
VL - 55
SP - 2276
EP - 2277
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 8
ER -