Table 1 Optimization of the reaction conditions.

From: Pyrinap ligands for enantioselective syntheses of amines

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Entry

Ligand

x (mol%)

Yield of 4aaaa

ee of 4aaa (%)b

1

(R,Sa)-L1

5

68

−78

2

(R,Sa)-L2

5

75

−84

3

(R,Ra)-L2

5

84

85

4c

(R,Ra)-L2

5

74

90

5c,d

(R,Ra)-L2

5

79

90

6c,d,e

(R,Ra)-L2

2.5

73 (70f)

90

7g

(S,S,Ra)-UCD-PHIM

1

84

−98

8h

(S,S,Ra)-UCD-PHIM

1

86

−85

  1. aDetermined by 1H NMR analysis with CH2Br2 as the internal standard.
  2. bDetermined by chiral HPLC analysis of the isolated product.
  3. cThe reaction was carried out at 0 °C.
  4. d1.2 equivalents of 2a and 3a were used.
  5. eThe reaction was conducted on 0.5 mmol scale.
  6. fIsolated yield.
  7. gData taken from ref. 32.
  8. hData produced in this laboratory using (S,S,Ra)-UCD-PHIM prepared in this laboratory.
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