Mechanistic studies of diastereoselective cyclopropanation via homochiral ketals. 1. Dioxolane structural effects

…, KA Nelson, PC Heidt, S Van Deusen

Index: Mash, Eugene A.; Hemperly, Susan B.; Nelson, Keith A.; Heidt, Philip C.; Deusen, Shawne Van Journal of Organic Chemistry, 1990 , vol. 55, # 7 p. 2045 - 2055

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Citation Number: 90

Abstract

Compounds structurally related to 2-cyclohexen-1-one 1, 4di-O-benzyl-~-threitol ketal were prepared and subjected to the Simmons-Smith cyclopropanation. From these experiments a mechanistic model for diastereoselective cyclopropanation of common ring systems (five-, six-, and seven-membered) has been formulated. Diastereoselectivity is thought to result from preferential chelation of the Simmons-Smith reagent at the least sterically hindered ...