Table 1 Addition of MeMgX reagents to β-hydroxyketones

From: Unmasking the halide effect in diastereoselective Grignard reactions applied to C4´ modified nucleoside synthesis

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entry

compound

[M]Me

solvent

product (ratio)a

yield syn-diol

1

6

MeMgCl

THF

13 (53%)b 

0%

2

7

MeMgCl

THF

10a:10b (1.1:1)

33%

3

7

MeMgCl

CH2Cl2

10a:10b (2.2:1)

48%

4

7

MeMgBr

CH2Cl2

10a:10b (6:1)

45%

5

7

MeMgI

CH2Cl2

10a:10b (7.8:1)

72%

6

7

MeMgI

THF

10a:10b (0.8:1)

17%

7

7

Me2Mg

CH2Cl2

10a:10b (1:1)

ND

8

8

MeMgCl

CH2Cl2

11a:11b (1:1)

43%

9

8

MeMgBr

CH2Cl2

11a:11b (2.5:1)

56%

10

8

MeMgI

CH2Cl2

11a:11b (5.5:1)

78%

11

9

MeMgCl

CH2Cl2

12a:12b (0.7:1)

21%

12

9

MeMgI

CH2Cl2

12a:12b (1.8:1)

58%

  1. aDetermined by analysis of 1H NMR spectra recorded on the crude reaction mixture;
  2. bOnly product produced.
  3. cND = not determined.
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