New methodology for the synthesis of α,α-dialkylamino acids using the "self-regeneration of stereocenters" Method: α-ethyl-α-phenylglycine

Heterocycles

Volumn 46, Issue 1, 1997, Pages 617-630

  O'Donnell, Martin J ^a   Fang, Zhiqiang ^a   Ma, Xiaojun ^a   Huffman, John C ^b  

^a INDIANA UNIVERSITY   (United States)

^b INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001713977     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-97-s83     Document Type: Article

References (76)

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66. See beginning of experimental section for methods for determination of levels of stereoselectivity in starting oxazolidinones (1, 2, and 8), and in alkylation products (3, 4, and 9). Note that starting materials (1) and (2) are diastereomers while products (3) and (4) are enantiomers.
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69. W(F) = 0.0727. Crystallographic details are available from http://www.iumsc.indiana.edu, entry 93248.
70. For comparative purposes, the price (Aldrich Catalog, 1996-1997, based on largest available quantity) of one mole of each reagent follows: CbzCl, $31.31; PhCOCl, $2.15.
71. The pKa's (DMSO) have been measured for the Cbz-oxazolidinones: 1, 18.0; 2, 18.1. We thank Professor F.G. Bordwell and Dr. X.-M. Zhang for conducting these experiments.
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75. The room temperature NMR spectra of the 4,4-disubstituted oxazolidinones are often quite complex. This is likely due to the presence of E- and Z-isomers from the carbamate (or amide) functionality. A detailed discussion for the related 5,5-disubstituted imidazolidinones is given in Ref. 9d, p. 148.
76. Kindly provided by Drs. J.-C. Caille and M. Bulliard of SIPSY S. A.