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. 2020 Dec 15;86(1):850–860. doi: 10.1021/acs.joc.0c02385

Table 2. Different Amines for the Asymmetric α-Allylation of 1a.

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entrya amine yield (%)b ee (%)c
1 A1 89 31 (S)
2 (R,R)-A2 98 94 (R)
3 (S,S)-A2 97 94 (S)
4 A3 89 37 (R)
5 A4 89 21 (R)
6 A5 90 60 (R)
7 A6 97 44 (R)
a

Performed on a 0.375 mmol scale by using 4.0 mol % Pd(PPh3)4, 50 mol % amine, 6.25 mol % P5, 190 mg 5 Å molecular sieves, and 0.75 mmol allyl alcohol in 0.75 mL MTBE at 60 °C for 16 h.

b

Determined by GC analysis.

c

Determined by chiral HPLC analysis using a Diacel Chiralcel AS-H column. Absolute configurations were determined by measuring the optical rotations and comparing with the literature data.