Asymmetric Oxidation of Alcohols and Phenol Derivatives with Air as Oxidant - Transition Metal Catalysis in Aerobic Alcohol Oxidation - page 243

R 2

R 2

R 1

11
(4 mol%)
air
h ν

H

OH

O

R 1

d n 4 r 4 n g | 1

R 1

O

OH

H

R 1

rt

R 2

R 2

R 1 = H, R 2 = H, 79%, 81% ee
R 1 = Me, R 2 = H, 66%, 72% ee
R 1 = H, R 2 = Me, 10%, 86% ee

( R )

N NO N

Ru

O
Ph

O

Cl

Ph

( R a)

11

Scheme 9.16 Enantioselective cyclization catalyzed by an Ru(salen) complex.

R

12 or 13
air OH

OH

2 R

OH

.

R

Gong et al. Sasai et al.

O

O

N

N

O

O

V

V

O
O

O
O

O
O

O
O

O

V

V

O

O

N

N

O

O

12 13

Scheme 9.17 Binuclear vanadium complex-catalyzed aerobic oxidative coupling of
2-naphthols.

In 2009, Egami and Katsuki reported the iron-catalyzed AOC of
2-naphthols with air (Scheme 9.18). 17a Iron(salan) complex 6 catalyzes the
highly enantioselective oxidative coupling of 2-naphthol derivatives that