Home Nonfiction 10 • Download Asymmetric Catalysis by B. Bosnich (auth.), B. Bosnich (eds.) PDF

Download Asymmetric Catalysis by B. Bosnich (auth.), B. Bosnich (eds.) PDF

By B. Bosnich (auth.), B. Bosnich (eds.)

The expense of strengthen in parts of technology is seldom consistent. often sure fields effloresce with task as a result of ~ealization that ideas are attainable to lengthy status very important difficulties. So it truly is now with uneven catalysis, a box which offers to alter profoundly the strategic contemplating man made chemists. As this file will express, reagents that can result in catalytic enantiocontrol of chemical modifications may possibly symbolize the final word artificial process. approximately all artificial recommendations of complicated molecules contain steps which require enantiocontrol and, in lots of situations, a particular catalytic transformation embodying enan­ tiocontrol has huge, immense merits when it comes to the speed and financial system of the response. simply because uneven catalysis is in a formative degree, staff with diversified backgrounds have joined the sector. This Workshop had representatives with organometallic, natural, structural, kinetic, enzymatic, microbiological and commercial backgrounds. every one had his personal point of view and this record represents a consensus of this team of 11 humans. the result's most likely as compre­ hensive and balanced a view of the topic as is feasible at the moment. it truly is was hoping that those that have in the past had yet a glancing curiosity in uneven catalysis will locate this document an invaluable indication of its current country. We think that uneven catalysis could have an expanding influence at the improvement of chemistry and may ultimately dominate a lot of artificial and business chemistry.

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106, 1331 (1976) . 4. H. Kumobayashi, S. Akutagawa and S. Otsuka, J. Am. Chern. , 102, 7932 (1980). 5. K. Tani, T. Yamagata, S. Otsuka, S. Akutagawa and H. S. Chern. , 600 (1982). 6. L. Jacobs and D. Daukner, J. Org. , 7. K. Tani, T. Yamagata, S. Akutagawa, H. Kumobayashi, T. Taketomi, H. Takaya, A. Miyashita, R. Noyori and S. Otsuka, J. Am. Chern. Soc. 106, 5208 (1984). 4. ~, 4036 (1981). ~, 1424 (1957). Asymmetric Hydrosilation Hydrosilation is the addition of a silicon-hydrogen bond across a double bond which can be homopolar C~C or heterpolar c=o or C=N.

Soc. Chern. , 612 (1983). 3. K. Stille and G. Parrinello, J. Mol. Catalysis, 21, 203 (1983). 2. ASYMMETRIC HYDROCARBOXYLATION Catalytic hydrocarboxylation (eq. 3) involves the conversion of an olefin into a carboxylic acid ester by the addition of CO and an alcohol. In a formal sense it resembles hydroformylation, >==< + CO + HX ++ (3 ) H COX in so far as both involve the addition of HX, where X=H for hydroformylation and where X = OR for hydrocarboxylation. As we shall see, there is also a mechanistic analogy.

10 4 11 P 2 PtCl/SnC1 2 Asymmetric Ligands Tested 23 Substrates Rh(I)/P 2 Catalyst Precursor 28 68 Examples Hydroformylation of Olefins having Prochiral Carbon Atoms. 2(S) 27(S) tJ Enantiomeric excess % 2-(acetoxyl)propanal) 51(R) 2-Methylbutanal 2-Phenylpropanal 2-Phenylpropanal Product DBDIOP = DIOP in which the diphenylphosphino groups on each phosphorus atom have been replaced by a 5H-dibenzo-phosphole group PtC1 2 /SnC1 2 Norbornene 60 (-) -DIOP PtCl/snC1 2 trans-2-Butene 25 HRh(CO) (PPh 3 )3 (-) -DIOP cis-2-Butene 80 (-) -DBPDIOP Rh (COD) acac Vinylacetate 60 (-)-DIOP 57 40 TOC PtC1 2 /snC1 2 BPPM (-) -DBPDIOP Asymmetric ligand I-Butene Ptc1 2 /snC1 2 Catalyst precursor Substrate Highest enantiomeric excess obtained in hydroformylation reactions TABLE 2 48.

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