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An Improved Synthesis of Cyclopropanes from Stabilized Phosphonates and 1,2-Dioxines

2002; American Chemical Society; Volume: 67; Issue: 9 Linguagem: Inglês

10.1021/jo0110496

1520-6904

Marc C. Kimber, Dennis K. Taylor,

Organic and Inorganic Chemical Reactions

Addition of stabilized Horner-Wadsworth-Emmons (HWE) phosphonates to substituted 1,2-dioxines leads to diastereomerically pure di- and trisubstituted cyclopropanes in high yields and represents a viable alternative to ylides in the cyclopropanation reaction involving 1,2-dioxines. While yields are comparable, reaction times with these stabilized phosphonates were accelerated and the diastereoselectivity for this cyclopropanation reaction was significantly greater than for the previously reported examples employing ylides.