By Ernest L. Eliel
content material: methods for uneven synthesis as directed towards traditional items / Barry M. Trost --
man made keep an eye on resulting in usual items / Teruaki Mukaiyama --
uneven synthesis of chiral tertiary alcohols in excessive enantiomeric extra / Ernest L. Eliel, Jorma okay. Koskimies, Bruno Lohri, W. Jack Frazee, Susan Morris-Natschke, Joseph E. Lynch, and Kenso Soai --
Acyclic stereoselection through the aldol condensation / Clayton H. Heathcock --
uneven carbon-carbon bond forming reactions through chiral chelated intermediates : diastereoselective uneven synthesis of 1,2-disubstituted cycloalkanecarboxaldehydes / Kenji Koga --
uneven carbon-carbon bond forming reactions through chiral oxazolines / Albert I. Meyers --
hugely selective synthesis with novel metal reagents / Hitosi Nozaki, Tamejiro Hiyama, Koichiro Oshima, and Kazuhiko Takai --
Novel techniques to the uneven synthesis of peptides / Iwao Ojima --
uneven carbon-carbon bond formation utilizing enantiomerically natural vinylic sulfoxides / Gary H. Posner, John P. Mallamo, Kyo Miura, and Martin Hulce --
uneven reactions : a problem to the commercial chemist / Gabriel Saucy and Noal Cohen --
Stereochemistry of heterogeneous uneven catalytic hydrogenation / Kaoru Harada --
uneven Grignard cross-coupling catalyzed via chiral phosphine-nickel and phosphine-palladium complexes / Tamio Hayashi --
Rhodium(I) catalyzed enantioselective hydrogen migration of prochiral allylamines / ok. Tani, T. Yamagata, S. Otsuka, S. Akutagawa, H. Kumobayashi, T. Taketomi, H. Takaya, A. Miyashita, and R. Noyori --
program of immobilized enzymes for uneven reactions / Ichiro Chibata --
uneven synthesis utilizing cofactor-requiring enzymes / George M. Whitesides, Chi-Huey Wong, and Alfred Pollak --
Mechanistic issues of biomimetic uneven savings / Atsuyoshi Ohno --
Stereochemistry of one-carbon move reactions / Heinz G. Floss --
an invaluable and comfortably available chiral desk bound section for the liquid chromatographic separation of enantiomers / William H. Pirkle, John M. Finn, Bruce C. abate, James Schreiner, and James R. Pribish --
New uneven reactions utilizing (S)-2-aminomethylpyrrolidine derivatives / Masatoshi Asami --
Liquid chromatographic answer of enantiomeric [alpha]-amino acid derivatives utilising a chiral diamide section / Shoji Hara, Akira Dobashi, and Masakatzu Eguchi --
uneven aid with chiral NADH version compounds / Yuzo Inouye --
uneven hydrogenation of cyclic dipeptides containing [alpha], [beta]-dehydroamino acid residues and next practise of optically natural [alpha]-amino acids / Nobuo Izumiya.
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Additional info for Asymmetric Reactions and Processes in Chemistry
We have s y n t h e s i z e d two p e r t i nent oxathianes, one (Jj>) d e r i v e d from (+)- or (-)-camphor-10s u l f o n i c a c i d (20) (Scheme 7) and the o t h e r (£) d e r i v e d from (+)-pulegone (21) (Scheme 8 ) . Both (+)- and (-)-camphorsulfonic a c i d s a r e a v a i l a b l e commercially, the l a t t e r i n form o f i t s ammonium s a l t . While the f r e e a c i d (a hemihydrate) i s d i f f i c u l t t o c h a r a c t e r i z e , the ammonium s a l t i s e a s i l y r e c r y s t a l l i z e d t o enantiomeric p u r i t y and c h a r a c t e r i z e d by s p e c i f i c r o t a t i o n .
J. Soc. H. Chem. ; Tramontini, M. -P. E. Soc. H. Tetrahedron Lett. 1980, 1031 and refs. there cited. 14. Dissertation, University of North Carolina, Chapel Hill, NC, 1981. 15. S. Soc. 1949, 3098. 16. ; Allenmark, S. Scripta 1974, 5, 13. 17. cf. W. "Protective Groups in Organic Synthesis"; Wiley-Interscience: New York, 1981; pp. 133-140. 18. ; Ogasawara, K. Chem. Commun. ; Jurion, M. ibid. 1972, 382. 19. -i. Bull. 1975, 23, 527. 20. J. Chem. 1979, 44, 3598. 21. E. Tetrahedron Lett. 1981, 22, 2855.
Our s y n t h e s i s o f (R)-(-)-mevalolactone (24) i s shown i n Scheme 10. The c r u c i a l i n t e r m e d i a t e , s y n t h e s i z e d by the e a r l i e r d e s c r i b e d method, i s (+)-2-methyl-3-butene-l,2-diol, Its oxathiane p r e c u r s o r was obtained i n 90% diastereomer excess, i n c r e a s e d t o 97% by one r e c r y s t a l l i z a t i o n . D i o l ^ was then con v e r t e d t o the monotosylate which y i e l d e d c h i r a l 3-hydroxy-3methyl-4-pentenonitrile, when heated with KCN/EtOH.
Asymmetric Reactions and Processes in Chemistry by Ernest L. Eliel