Table 1 Establishment of the organocatalytic multicomponent allylation.

From: Efficient access to general α-tertiary amines via water-accelerated organocatalytic multicomponent allylation

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Entry

Acid catalyst (5 mol%)

Reaction medium

Activator (5 mol%)

Additive (x equiv.)

Yield (%)

4a

5

1

-

H2O-NaCl (sat.)

-

-

n.d.

22

2

(S)-BINOL

H2O-NaCl (sat.)

-

-

n.d.

30

3

BzOH

H2O-NaCl (sat.)

-

-

<5

24

4

Erucic acid

H2O-NaCl (sat.)

-

-

n.d.

32

5

(±)-PA

H2O-NaCl (sat.)

-

-

46

15

6

Tf2NH

H2O-NaCl (sat.)

-

-

63

20

7

ScTS

H2O-NaCl (sat.)

-

-

67

24

8

TfOH

H2O-NaCl (sat.)

-

-

9

22

9

PFBS

H2O-NaCl (sat.)

-

-

43

23

10

Nafion

H2O-NaCl (sat.)

-

-

27

25

11

4-SCA

H2O-NaCl (sat.)

-

-

14

34

12

PTSA

H2O-NaCl (sat.)

-

-

3

25

13

DBSA

H2O-NaCl (sat.)

-

-

62

12

14

DBSA

H2O

-

-

77

3

15

DBSA

PhMe

-

-

45

n.d.

16

DBSA

H2O

-

PhMe (5)

81

2

17

DBSA

H2O

SQA-III

-

88

4

18

-

H2O

SQA-III

PhMe (5)

1

8

19

DBSA

H2O

SQA-I

PhMe (5)

83

2

20

DBSA

H2O

SQA-II

PhMe (5)

17

6

21

DBSA

H2O

SQA-III

PhMe (5)

96

4

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  1. aConditions: Reactions were performed using ketone 1a (0.2 mmol), benzhydrazide 2a (1.2 equiv.), allylboronic acid pinacol ester 3a (1.5 equiv.), and a set of catalysts (5.0 mol%) in medium (2.0 mL: 10 L/mol (1a)) and additive (5.0 equiv.) at 60 °C for 24 h. bYields were determined by 1H NMR analysis using 1,3,5-trimethoxybenzene as the internal standard. cn.d. = not detected. Bz = benzoyl; cat. = catalyst; Et = ethyl.
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