Fig. 2: Dearomative 3,4-dual functionalization of aryl sulfoxides.
From: Dearomative di- and trifunctionalization of aryl sulfoxides via [5,5]-rearrangement
Reactions were performed under optimal conditions given in Table 1, entry 15. Base (4-ethylmorpholine) and Nu were added in sequence (4u-4y, 4a′, 4b′, 6j and 6k) or in one portion (others). For cases given below dashed line, sily enol ether 3a or vinyl zinc chloride 3t were used as nucleophile. Unless otherwise noted, only one diastereoisomer was obtained. dr = diastereoisomeric ratio. [b] The absolute configuration of major isomer of 4n is not confirmed. [c] Nu (3.0 equiv) was used. [d] 4-Ethylmorpholine (4.0 equiv) was used. [e] Tf2O, −55 °C, 36 h. [f] DIPEA instead of 4-ethylmorpholin was used. [g] Nu, −95 °C, 12 h. [h] 2a (10 equiv) was used. [i] 6k and 6l were contaminated with small amounts of inseparable 1,2-addition products 6k′ and 6l′ with 86/14 rr and 83/17 rr, respectively. [j] In lieu of 6p and 6q, aryl sulfides 7 and 8 were obtained in 40% and 80% yields, respectively.
