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By Ernest L. Eliel

content material: ways for uneven synthesis as directed towards average items / Barry M. Trost --
artificial regulate resulting in traditional 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 ways 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 economic chemist / Gabriel Saucy and Noal Cohen --
Stereochemistry of heterogeneous uneven catalytic hydrogenation / Kaoru Harada --
uneven Grignard cross-coupling catalyzed by means of chiral phosphine-nickel and phosphine-palladium complexes / Tamio Hayashi --
Rhodium(I) catalyzed enantioselective hydrogen migration of prochiral allylamines / okay. 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 rate reductions / Atsuyoshi Ohno --
Stereochemistry of one-carbon move reactions / Heinz G. Floss --
an invaluable and comfortably available chiral desk bound part 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 utilizing a chiral diamide part / Shoji Hara, Akira Dobashi, and Masakatzu Eguchi --
uneven relief with chiral NADH version compounds / Yuzo Inouye --
uneven hydrogenation of cyclic dipeptides containing [alpha], [beta]-dehydroamino acid residues and next guidance of optically natural [alpha]-amino acids / Nobuo Izumiya.

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Woodward c h a r a c t e r i z e d the macrolide a n t i b i o t i c erythromycin as a s y n t h e t i c challenge which i s " . . q u i t e h o p e l e s s l y complex, e s p e c i a l l y i n view o f i t s p l e t h o r a o f asymmetric c e n t e r s . ; ACS Symposium Series; American Chemical Society: Washington, DC, 1982. ch004 molecule and the above mentioned quote from the master o f organic s y n t h e s i s which planted the seed o f the p r o j e c t which i s discussed i n t h i s a r t i c l e .

I. Bull. 1975, 23, 527. 20. J. Chem. 1979, 44, 3598. 21. E. Tetrahedron Lett. 1981, 22, 2855. 22. L. unpublished observations. ; ACS Symposium Series; American Chemical Society: Washington, DC, 1982. 3. ELIEL ET AL. ch003 23. 24. 25. 26. L. unpublished observations. ; Soai, K. Tetrahedron Lett. 1981, 22, 2859. W. Chem. 1971, 36, 3553. ; Konno, K. (London) 1964, 233. 27. Regarding previous reports on chiral 10a and 10b, cf. J. Chem. H. Soc. 1951, 73, 2391. 28. ; Asami, M. Lett. 1978, 1253; 1979, 705.

3. ELIEL 49 Chiral Tertiary Alcohols E T AL. ch003 Scheme 7 7^ *7 S ^R R'MgX 1) BuLi, RCHO 'OH 2) DMSO- TFAA-EtjN (CH 0) 1 2 X TsOH A SH R R I . β. e. ; ACS Symposium Series; American Chemical Society: Washington, DC, 1982. ch003 50 ASYMMETRIC REACTIONS A N D PROCESSES IN CHEMISTRY Experiments p r e s e n t l y i n progress suggest t h a t the monot o s y l a t e p r e c u r s o r s of the t e r t i a r y a l c o h o l s can a l t e r n a t i v e l y be converted, by base, t o p r i m a r y - t e r t i a r y epoxides which i n t u r n may be opened a t the primary s i t e by a v a r i e t y o f n u c l e o p h i l e s , thus g r e a t l y a m p l i f y i n g the o p p o r t u n i t i e s f o r s y n t h e s i s o f compounds bearing c h i r a l t e r t i a r y c a r b i n o l m o i e t i e s .

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