Table 1 Optimization of the reaction conditionsa.

From: Mild synthesis of isoxazoline derivatives via an efficient [4 + 1] annulation reaction of transient nitrosoalkenes and sulfur ylides

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Entry

X

Solvent

Base (equiv.)

Yieldb (%)

1

Br

CH2Cl2

K2CO3 (1.2)

71

2

Br

CHCl3

K2CO3 (1.2)

80

3

Br

Et2O

K2CO3 (1.2)

62

4

Br

DMSO

K2CO3 (1.2)

26

5

Br

toluene

K2CO3 (1.2)

37

6

Br

CHCl3

Na2CO3 (1.2)

89

7

Br

CHCl3

NaOH (1.2)

48

8

Br

CHCl3

t-BuOK (1.2)

38

9

Br

CHCl3

Et3N (1.2)

20

10

Br

CHCl3

Na2CO3 (1.3)

91

11c

Br

CHCl3

Na2CO3 (1.3)

94

12c

Cl

CHCl3

Na2CO3 (1.3)

83

  1. aReaction conditions: 1a (0.40 mmol), 2a (0.48 mmol), solvent (4 mL), base. bYield of isolated product. cThe ratio of 1a or 1aʹ and 2a is 1:1.3. DMSO: dimethyl sulfoxide.