Table 1 Acceleration effect for 3-aza-Cope rearrangement by catalysts under different conditionsa

From: Chiral BINOL-phosphate assembled single hexagonal nanotube in aqueous solution for confined rearrangement acceleration

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No.

R

Catalyst

Solvent

kobs 10−5 s−1

Acceleration

1

H

Blank

DMSO-d6/D2Ob

2.6

―

2

H

Nanotube

DMSO-d6/D2O

43.5

17

3

H

Cat1

DMSO-d6

6.0

2.3

4

H

Crystalc

DMSO-d6/D2O

2.8

1.1

5

H

Cat2

DMSO-d6/D2O

4.2

1.6

6

Me

Blank

DMSO-d6/D2O

6.4

―

7

Me

Nanotube

DMSO-d6/D2O

545.0

85

8

Me

Cat1

DMSO-d6

32.6

5.1

9

Me

Crystal

DMSO-d6/D2O

8.1

1.3

10

Me

Cat2

DMSO-d6/D2O

15.3

2.4

  1. aReaction conditions: substrate (2.8 mM), catalyst (5.6 mM), solvent (600 μL), pD = 8.0, 50 °C, the reaction was conducted in NMR tube and monitored by NMR spectroscopy.
  2. bDMSO-d6/D2O: v/v = 1/2.
  3. cThe nanotube crystal cannot redissolve into the aqueous solution.
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