Tetrahedron Letters p. 9241 - 9244 (2001)
Update date:2022-07-30
Topics: Asymmetric synthesis Optically active 1-chlorovinyl p-tolyl sulfoxides
Satoh, Tsuyoshi
Yoshida, Masaaki
Ota, Hiroyuki
Treatment of optically active 1-chlorovinyl p-tolyl sulfoxides having two different substituents at the 2-position, which were synthesized from unsymmetrical ketones and (R)-(-)-chloromethyl p-tolyl sulfoxide in three steps, with cyanomethyllithium gave optically active 2-amino-1-cyano-5,5-disubstituted-1,3-cyclopentadienes with very high asymmetric induction from the sulfoxide chiral center. The products were converted to the enantiomerically pure 4,4-disubstituted 2-cyclopentenones by heating with phosphoric acid in acetic acid.
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