TY - JOUR
T1 - Asymmetric spirocyclization
T2 - A new type of acid-catalyzed intramolecular 1,4-addition to form carba-spirocyclic compounds
AU - Yamada, Satoshi
AU - Karasawa, Satoru
AU - Takahashi, Youichi
AU - Aso, Mariko
AU - Suemune, Hiroshi
PY - 1998/12/17
Y1 - 1998/12/17
N2 - Novel spirocyclization based on intramolecular 1,4-addition and its asymmetric version have been developed using a combination of Lewis acid and 1,2-diol. Treatment of five- and six-membered α,β-unsaturated cyclic ketones having a 4-oxopentyl group at the β-position with Lewis acid and ethylene glycol gave spiro[4.5]decane-2,7-dione and spiro[5.5]undecane-2,8- done, respectively. The asymmetric version of this reaction has been developed by using optically active 1,2-diol such as cyclohexane-1,2-diol to afford the spirocyclic products of up to 85% e.e.
AB - Novel spirocyclization based on intramolecular 1,4-addition and its asymmetric version have been developed using a combination of Lewis acid and 1,2-diol. Treatment of five- and six-membered α,β-unsaturated cyclic ketones having a 4-oxopentyl group at the β-position with Lewis acid and ethylene glycol gave spiro[4.5]decane-2,7-dione and spiro[5.5]undecane-2,8- done, respectively. The asymmetric version of this reaction has been developed by using optically active 1,2-diol such as cyclohexane-1,2-diol to afford the spirocyclic products of up to 85% e.e.
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U2 - 10.1016/S0040-4020(98)01009-6
DO - 10.1016/S0040-4020(98)01009-6
M3 - Article
AN - SCOPUS:0032542152
VL - 54
SP - 15555
EP - 15566
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 51
ER -