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Asymmetric Hydroformylation of Vinylfurans Catalyzed by {(11bS)-4-{[(1R)-2′-Phosphino[1,1′-binaphthalen]-2-yl]oxy}dinaphtho[2,1-d:1′,2′-f]- [1,3,2]dioxaphosphepin}rhodium(I) [RhI{(R,S)-binaphos}] Derivatives

✍ Scribed by Koji Nakano; Ryo Tanaka; Kyoko Nozaki

Book ID
102253448
Publisher
John Wiley and Sons
Year
2006
Tongue
German
Weight
90 KB
Volume
89
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The asymmetric hydroformylation of 2‐ and 3‐vinylfurans (2a and 2b, resp.) was investigated by using [Rh{(R,S)‐binaphos}] complexes as catalysts ((R,S)‐binaphos = (11b__S__)‐4‐{[1__R__)‐2′‐phosphino[1,1′‐binaphthalen]‐2‐yl]oxy}dinaphtho[2,1‐d:1′,2′‐f][1,3,2]dioxaphosphepin; 1). Hydroformylation of 2 gave isoaldehydes 3 in high regio‐ and enantioselectivities (Scheme 2 and Table). Reduction of the aldehydes 3 with NaBH~4~ successfully afforded the corresponding alcohols 5 without loss of enantiomeric purity (Scheme 3).

📜 SIMILAR VOLUMES

Encyclopedia of Reagents for Organic Syn
Encyclopedia of Reagents for Organic Synthesis || (11b R )-4-Hydroxy-2,6-bis[2,4,6-tris(1-methylethyl)phenyl]-dinaphtho[2,1- d : 1′,2′- f ][1,3,2]dioxaphosphepin-4-oxide, [( R )-TRIP] & (11b S )-4-Hydroxy-2,6-bis[2,4,6-tris(1-methylethyl)phenyl]-dinaphtho[2,1- d : 1′,2′- f ][1,3,2]dioxaphosphepin-4-oxide, [( S )-TRIP]
✍ Hutchinson, Douglas K. 📂 Article 📅 2013 🏛 John Wiley & Sons, Ltd 🌐 English ⚖ 186 KB

Contains A Database Of Approximately 70,000 Reactions And 4000 Of The Most Frequently Consulted Reagents. Fully Searchable By Structure And Sub-structure, Reagent, Reaction Type, Experimental Conditions, And Keyword. Also Includes A Searchable Interface: Acronym Finder (an Interface For Scientific A