TY - JOUR
T1 - Geometry‐Directed Generation and Synthetic Application of α‐Lithio Oxime Ethers
AU - Shatzmiller, Shimon
AU - Lidor, Rami
AU - Shalom, Eytan
AU - Bahar, Naim Menashe Eliezer
PY - 1989
Y1 - 1989
N2 - Several mono‐ and di‐O‐alkyloximes have been regioselectively transformed to the syn α‐lithio derivatives by treatment with n‐butyllithium. The control of oxime ether geometry served to control regioselectivity in α‐lithiation and subsequent carbon‐carbon (alkylation, oxidative coupling) and carbon‐halogen bond formation reactions. The geometry‐directed α‐lithiation‐dimerization sequence was used for the synthesis of large ring compounds.
AB - Several mono‐ and di‐O‐alkyloximes have been regioselectively transformed to the syn α‐lithio derivatives by treatment with n‐butyllithium. The control of oxime ether geometry served to control regioselectivity in α‐lithiation and subsequent carbon‐carbon (alkylation, oxidative coupling) and carbon‐halogen bond formation reactions. The geometry‐directed α‐lithiation‐dimerization sequence was used for the synthesis of large ring compounds.
UR - http://www.scopus.com/inward/record.url?scp=85005688675&partnerID=8YFLogxK
U2 - 10.1002/ijch.198900026
DO - 10.1002/ijch.198900026
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AN - SCOPUS:85005688675
SN - 0021-2148
VL - 29
SP - 187
EP - 194
JO - Israel Journal of Chemistry
JF - Israel Journal of Chemistry
IS - 2-3
ER -