An Unanticipated Result in the Pd (0) Catalyzed Coupling of Sodium Adenate with cis-4-Acetyloxy- and cis-4-t-Butyldimethylsilyloxy-2-Cyclopentenyl Diethylphosphate

Abstract

The preparation of adenine regioisomers of (+/-)-cis-4-(TBSO)-and (+/-)-cis-4-(AcO)-2-cyclopentene is described using either Pd(0) coupling (silyl ether 2) or chloride displacement (acetyl chloride 10). An unexpected difference in reactivity between TBS- and Ac-O-protected allyl phosphates 2 and 7 in Pd(0) catalyzed coupling with sodium adenate was observed.