TY - JOUR
T1 - Asymmetric synthesis of methylenecyclobutanes and their transformation to medium-sized carbocyclic compounds
AU - Narasaka, Koichi
AU - Hayashi, Kazuhiro
AU - Hayashi, Yujiro
PY - 1994/4/11
Y1 - 1994/4/11
N2 - The catalytic asymmetric [2+2] cycloaddition proceeds between 3-(2-alkenoyl)-1, 3-oxazolidin-2-ones and 1, 2-propadienyl sulfides having various substituents at 1-position, affording methylenecyclobutane derivatives with high optical purity. Seven and eight membered carbocycles with chiral side chains are prepared by the ring cleavage reaction and successive cationic cyclization of the chiral methylenecyclobutane derivatives having ω-alkenyl substituents.
AB - The catalytic asymmetric [2+2] cycloaddition proceeds between 3-(2-alkenoyl)-1, 3-oxazolidin-2-ones and 1, 2-propadienyl sulfides having various substituents at 1-position, affording methylenecyclobutane derivatives with high optical purity. Seven and eight membered carbocycles with chiral side chains are prepared by the ring cleavage reaction and successive cationic cyclization of the chiral methylenecyclobutane derivatives having ω-alkenyl substituents.
KW - catalytic asymmetric [2+2] cycloaddition reaction
KW - cationic cyclization
KW - chiral titanium reagent
KW - methylenecyclobutanes
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U2 - 10.1016/S0040-4020(01)89384-4
DO - 10.1016/S0040-4020(01)89384-4
M3 - Article
AN - SCOPUS:0028222654
SN - 0040-4020
VL - 50
SP - 4529
EP - 4542
JO - Tetrahedron
JF - Tetrahedron
IS - 15
ER -