Diastereoselection during 1,2-Addition of the Allylindium Reagent to α-Thia and α-Amino Aldehydes in Aqueous and Organic Solvents

Journal of Organic Chemistry

Volumn 62, Issue 13, 1997, Pages 4293-4301

  Paquette, Leo A ^a   Mitzel, Thomas M ^a,b   Isaac, Methvin B ^a   Crasto, Curtis F ^a   Schomer, William W ^a  

^a OHIO STATE UNIVERSITY   (United States)

^b TRINITY COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000126518     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970274d     Document Type: Article

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70. Much of the specific information associated with the first two pathways originally appeared in the Ph.D. Thesis of M. W. Drewes, Universität Marburg, 1988, and the Diplomarbeit of A. Schmitz, Universität Marburg, 1987. We thank Prof. M. Reetz for providing us with excerpts from these documents.
71. This phenomenon was previously noted by A. Wehrsig, Ph.D. Dissertation, Universität Hamburg, 1991.
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75. 13b,14,15,33 Whereas methyl Grignard additions gave a 1.9:1 ratio of syn and anti products, methyl cuprate additions occurred with high syn selectivity (99%).
76. For the isoindoline compounds 42 and 43, Reetz has reported cuprate additions to occur with good syn selectivity (>90%).
77. For generic experimental details, see: Paquette, L. A.; Lobben, P. C. J. Am. Chem. Soc. 1996, 118, 1917.