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. 2023 May 2;14(21):5712–5721. doi: 10.1039/d3sc01637d

Initial screening of CPAsa.

graphic file with name d3sc01637d-u1.jpg
Entry CPA Time (h) Yield of 3aab (%) endo/exoc eec (%)
1 (R)-4a 12 95 81 : 19 71/88
2 (R)-4b 36 95 88 : 12 5/−12
3 (R)-4c 36 67 87 : 13 5/−3
4 (R)-5 20 95 74 : 26 71/NDd
5 (S)-6 74 62 99 : 1 88/NDd
6e (S)-6 5 d 91 99 : 1 92/NDd
a

Unless otherwise noted, all reactions were carried out using 0.1 mmol of 1a, 0.12 mmol of 2a, and 0.010 mmol of CPA catalyst (10 mol%) in toluene (1 mL).

b

Isolated yield.

c

Diastereomeric and enantiomeric excess were determined by chiral stationary phase HPLC analysis.

d

ND: not determined.

e

MS 5A (50 mg) was used as an additive.