Industrially viable syntheses of highly enantiomerically enriched 1-aryl alcohols via asymmetric hydrogenation

被引：44

作者：

Chaplin, D ^{[1
]}

Harrison, P ^{[1
]}

Henschke, JP ^{[1
]}

Lennon, IC ^{[1
]}

Meek, G ^{[1
]}

Moran, P ^{[1
]}

Pilkington, CJ ^{[1
]}

Ramsden, JA ^{[1
]}

Watkins, S ^{[1
]}

Zanotti-Gerosa, A ^{[1
]}

机构：

[1] Chirotech Technol Ltd, Cambridge CB4 0WG, England

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2003年 / 7卷 / 01期

关键词：

D O I：

10.1021/op025585r

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The practicalities of the asymmetric hydrogenation of acetophenone derivatives are addressed. The catalysts used, derived from the precatalysts [(xylylPhanePhos)RuCl2(DPEN)] (S)-(R,R)-1 and (R)-(SS)-1, were shown to possess very high reactivity. 4'-Fluoroacetophenone was hydrogenated at a molar substrate-to-catalyst ratio (S/C) of 100,000 with complete conversion effected in as little as 80 min (average turnover similar to1200 min(-1), peak turnover similar to2500 min(-1)). The catalysts are tolerant of a range of commercial grade substrates, in most cases a S/C of 5000-10000 was achieved without the need to purify the ketone. Using precatalyst 1 enantioselectivities of 95 --> 99% ee were achieved. The high selectivity and catalyst activity, plus the simplicity of the process, offers significant advantages over other enantioselective ketone reductions.

引用

页码：89 / 94

页数：6

共 22 条

[1] EFFECTIVE ASYMMETRIC HYDROBORATION CATALYZED BY A RHODIUM COMPLEX OF 1-(2-DIPHENYLPHOSPHINO-1-NAPHTHYL)ISOQUINOLINE [J].