Productive Asymmetric Synthesis of All Four Diastereomers of 3-(trans-2-Nitrocyclopropyl)alanine from Glycine with (S)- or (R)-2-[(N-Benzylprolyl)amino]benzophenone as a Reusable Chiral Auxiliary

All four diastereomers of 3‐(trans‐2‐nitrocyclopropyl)alanine (3) were prepared by asymmetrically induced α‐C alkylation of the glycine moiety in the [(S)‐ or (R)‐Schiff base]NiII complex 7, employing racemic trans‐1‐(iodomethyl)‐2‐nitrocyclopropane (8) as the alkylating agent. A notable difference...

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Bibliographic Details
Published in:	European journal of organic chemistry Vol. 2003; no. 5; pp. 869 - 877
Main Authors:	Larionov, Oleg V., Savel'eva, Tatyana F., Kochetkov, Konstantin A., Ikonnokov, Nikolai S., Kozhushkov, Sergei I., Yufit, Dmitrii S., Howard, Judith A. K., Khrustalev, Viktor N., Belokon, Yuri N., de Meijere, Armin
Format:	Journal Article
Language:	English
Published:	Weinheim WILEY-VCH Verlag 01-03-2003 WILEY‐VCH Verlag
Subjects:	Amino acids Asymmetric synthesis Chiral auxiliaries Nickel Nitrocyclopropylalanine
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Summary:	All four diastereomers of 3‐(trans‐2‐nitrocyclopropyl)alanine (3) were prepared by asymmetrically induced α‐C alkylation of the glycine moiety in the [(S)‐ or (R)‐Schiff base]NiII complex 7, employing racemic trans‐1‐(iodomethyl)‐2‐nitrocyclopropane (8) as the alkylating agent. A notable difference in solubility between the two diastereomeric products 9a/9b [when (S)‐7 was used as starting material] or 9d/9e [when (R)‐7 was employed] allowed for their separation from the same reaction mixture. All the diastereomers of 3‐(trans‐2‐nitrocyclopropyl)alanine (3) were produced upon brief exposure of the alkylation products 9 to dilute hydrochloric acid, with subsequent purification by ion‐exchange chromatography and crystallization. The absolute configurations of the nickel complexes 9a−e were established by X‐ray crystallographic analyses. In addition, the X‐ray crystal structure of (2S,1′S,2′R)‐3 was determined to confirm the convergence of the configurations of the parent nickel complexes 9 with those of the amino acids 3 derived from them. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
Bibliography:	ArticleID:EJOC200390131 ark:/67375/WNG-37XV2NTL-Q istex:1B56AD41430825B5711267925A84996BFC22BCF0
ISSN:	1434-193X 1099-0690
DOI:	10.1002/ejoc.200390131