The Journal of organic chemistry

Origin of Stereocontrol in the Construction of the 12-Oxatricyclo [6.3. 1.02, 7] dodecane Ring System by Prins− Pinacol Reactions

LE Overman, PS Tanis

Index: Overman, Larry E.; Tanis, Paul S. Journal of Organic Chemistry, 2010 , vol. 75, # 2 p. 455 - 463

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Citation Number: 9

Abstract

Polycyclic products containing the 12-oxatricyclo [6.3. 1.02, 7] dodecane moiety having either the trans (8a− e) or cis (9a− e) relative configuration of the oxacyclic bridge and the cis angular substituents are formed stereospecifically by Prins− pinacol cyclizations of unsaturated α-dithianyl acetals 14a− e or 15a− e. These results show that the topography (boat or chair) of the Prins cyclization of the sulfur-stabilized oxocarbenium ions generated ...