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. 2018 Jun 4;9(26):5767–5772. doi: 10.1039/c8sc02041h

Table 4. Effect of α-substituent on coumarins in enantioselective allylic alkylation a .

Inline graphic
Entry X t [h] 3 Yield b [%] er c
1 CN (1a) 36 3aa 86 98 : 2
2 CONH2 (1i) 36 3ia 81 98 : 2
3 CO2Et (1j) 48 3ja 80 97.5 : 2.5
4 CO2Bn (1k) 48 3ka 85 98 : 2
5 CO2H (1l) 42 3la <5 d
6 H (1m) 48 3ma <5

aReaction conditions: 3 mol% [Ir(COD)Cl]2, 6 mol% L1, 0.24 mmol of 1, 0.2 mmol of 2a and 0.2 mmol of DABCO in 0.6 mL CH2Cl2. The catalyst was prepared via n-PrNH2 activation.

bYields correspond to the isolated product after chromatographic purification.

cer was determined by HPLC analysis on a chiral stationary phase.

d 1m was isolated in 52% yield.