We also explored the scope of nucleophiles for the second substitution (Scheme 3). From triol 1a, various C-C bonds could be formed in the second substitution reaction under Tsuji-Trost conditions. In particular, malonitrile (2o), diketone (2p), cyanoester (2q) and -nitrosulfone (2r) led to the desired products having a new C-C bond. As expected, no diastereoselectivity was observed in the case of 2q and 2r. Interestingly, using Meldrum acid as the nucleophile, a double Tsuji-Trost reaction occurred, with Meldrum acid reacting twice (2s). New C-N bonds could be formed using amine nucleophiles. In particular, secondary amines led to the formation of products 2t-2w in good yields. Primary amines such as benzylamine could also react, albeit providing lower yield (2x). Phthalimide was also a suitable N-nucleophile, leading to a protected primary amine 2y. The use of sulfinates as nucleophile afforded sulfones 2z-2aa, through formation of a C-S bond. In particular, sulfone 2aa has the required benzothiazole substituent for the modified Julia olefination. Scheme 3. Scope of nucleophiles for the second allylic substitution. Reactions were carried out using 1a (0.4 mmol), trimethyl orthoacetate (0.6 mmol), BF3•Et2O (0.08 mmol) in DCM, then [Pd(allyl)Cl]2 (0.02 mmol), XantPhos (0.04 mmol) and a solution of nucleophile (0.8 mmol in 1 mL THF) were added in the same pot.