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. 2019 Oct 1;25(64):14555–14571. doi: 10.1002/chem.201903095

Table 3.

Hydrothiolation reactions of d‐ and l‐hexoglycals.

graphic file with name CHEM-25-14555-g028.jpg

Entry

Alkene

+thiol

Product

Temp.

Yield [%][a]

Ratio A:B

1

8+20

(1.2 equiv)

graphic file with name CHEM-25-14555-g029.jpg

rt

80

1.3:1[b]

2

−80 °C

76

8.5:1

3

−120 °C

75

6:1

4

9+20

(1.2 equiv)

graphic file with name CHEM-25-14555-g030.jpg

0 °C

67

2.3:1

5

−40 °C

95

1.5:1

6

−80 °C

95

1:1.2

7

−120 °C

95

1:1.2

8

10+20

(1.2 equiv)

graphic file with name CHEM-25-14555-g031.jpg

rt

38

1:0[b]

9

−80 °C

92

1:0

10

11+20

(1.2–2.0 equiv)

graphic file with name CHEM-25-14555-g032.jpg

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66

2.5:1[c]

11

−80 °C

81

5.5:1[d]

[a] Combined isolated yield; [b] data are taken from Ref. 23, 6 equiv, of thiol was used; [c] 2.0 equiv of thiol was used. [d] 1.2 equiv of thiol was used.