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Table 2 Screening of solvents in acetylation of diol 5 mediated by lipase TLa

From: Studies on lipase-catalyzed asymmetric synthesis of (S)-(hydroxymethyl)glutamic acid (HMG)

Entry

Solvent (log P)

Time (h)

Isolated yield (%)

Ee of 6 (%)f

1b

CH2Cl2 (1.25c)

72

30

76

2

Hexane (3.5c)/THF (0.49d) (1:1)

14

32

63

3

iPr2O (1.9d)

48

50

62

4

Benzene (2.0c)

15

60

38

5

Vinyl acetate (0.629 ± 0.286e)

2.5

63

64

  1. aTwo equiv of vinyl acetate (except for entry 5), and a same amount of lipase, as diol 5, were used
  2. bSame reaction shown in Table 1, entry 8
  3. cTaken from the recent paper by Salihu and Alam (2015)
  4. dTaken from Lee’s paper (Lee et al. 2004)
  5. eA calculated value taken from SciFinder Scholar (April 17, 2015)
  6. fDetermined by chiral HPLC analysis
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