Page 117 - Catalysts for Fine Chemical Synthesis Vol 1 - Robert & Poignant

Catalysts for Fine Chemical Synthesis: Hydrolysis, Oxidation and Reduction. Volume 1
Edited by Stan M Roberts and Geraldine Poignant
Copyright  2002 John Wiley & Sons, Ltd.
ISBN: 0-471-98123-0

7 Asymmetric Hydroxylation and
Aminohydroxylation

CONTENTS
7.1 Asymmetric aminohydroxylation of 4-methoxystyrene
P. O'Brien, S.A. Osborne and D.D. Parker. . . . . . . . . . . . 103
7.1.1 Conclusion . . . . . . . . . . . . . . . . . . . . . 105
7.2 Asymmetric dihydroxylation of (1-cyclohexenyl)acetonitrile
Jean-Michel VatE Á le . . . . . . . . . . . . . . . . . . 105
7.2.1 (R,R)-(1,2-Dihydroxycyclohexyl)acetonitrile acetonide. . . . . . . . 107
7.2.2 Conclusion . . . . . . . . . . . . . . . . . . . . . 108
References . . . . . . . . . . . . . . . . . . . . . . . 108

7.1 ASYMMETRIC AMINOHYDROXYLATION OF
4-METHOXYSTYRENE

P. O'Brien, S.A. Osborne and D.D. Parker
Department of Chemistry, University of York, Heslington, York YO10 5DD, UK

3.1eq t BuO 2 CNH 2 , 3.05 eq NaOH NHBoc
3.05 eq t BuOCl
OH
4 mol% K 2 OsO 2 (OH) 4
MeO
6 mol% (DHQ) 2 PHAL
MeO
2:1 n PrOH-water, 0 8C, 1h (S)
Materials and equipment

. tert-Butyl carbamate, 545 mg, 4.65 mmol
. n-Propanol, 24.2 mL
. Sodium hydroxide, 183 mg, 4.6 mmol
. Water, 12.2 mL
. tert-Butylhypochlorite, freshly prepared, 0.53 mL, 4.6 mmol
tert-Butyl hypochlorite was freshly prepared according to the literature
procedure [1,2] using sodium hypochlorite (5 % chlorine, purchased from
Acros Organics, catalogue number 41955). The quality of the sodium