Table 2 Substituent effects on NHC-Ni catalyzed diastereodivergent reductive hydroalkenylation of enyne with allyl Za.

From: NHC-Ni catalyzed 1,3- and 1,4-diastereodivergent heterocycle synthesis from hetero-substituted enyne

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Entry

2

Z

R1

Ligand

Product

Syn:Anti 5:5′

Syn:Anti 6:6′

Yield (%)

1

2a

O

Ph

IPr

SIPr

5′a

8:92

21:79

n.a.

78

32

2

2b

 

Me

IPr

5′b

11:89

 

64

3

2c

NH

Ph

IPr

5′c

3:97b

n.a.

51

4

2d

 

Me

IPr

5′d

7:93

 

76

5

2e

NMs

Ph

IPr

6e

n.a.

93:7b

73

    

SIPr

  

85:15b

21

6

2f

 

Me

IPr

6f

 

94:6

72

  1. a See Methods section for procedure. Homo-dimerization and oligomerization were obtained in some ineffective cases. Products were shown in relative configuration only.
  2. b By GCMS.
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