Chemistry Reference
In-Depth Information
10 mol %
i
-Pr
i
-Pr
Ar = 2,4,6-(i-Pr)
3
C
6
H
2
N
Ar
Me
O
Mo
O
Ph
Me
O
O
Me
Ar
O
Me
Me
Me
3a
90% conv, 70% yield
90% ee
Et
2
O, 22°C, 6 h
15 mol %
i
-Pr
i
-Pr
N
Ar = 2,4,6-(i-Pr)
3
C
6
H
2
Ar
Me
O
Mo
O
Ph
Me
O
O
O
Ar
Me
Me
Me
Me
CO
2
Me
CO
2
Me
3a
>98% conv, 94% yield
94% ee
C
6
H
6
, 22°C, 17 h
Scheme 8E.6.
Enantioselective synthesis of cyclic enol ethers bearing tertiary and all-carbon
quaternary stereogenic centers through Mo-catalyzed enantioselective RCM.
O
O
1) 1 N HCl (20% in THF)
O
2) 5 mol % TPAP, NMO
Me
Me
Me
Me
(83% ee)
67% yield (2 steps),
1:1 dr, 83% ee
O
1) AD-mix , MeSO
2
NH
2
O
O
OH
2) Dess-Martin periodinane
Me
Me
Me
Me
(83% ee)
69% yield (2 steps),
>95:5 dr, 83% ee
Scheme 8E.7.
Site-selective functionalization of products from enantioselective RCM of enol
ethers.
