Amination of grignard reagents with retention of configuration.

[see reaction]. The stereochemistry of electrophilic amination has been probed using the chiral Grignard reagent 5, in which the magnesium-bearing carbon atom is the sole stereogenic center. Amination with azidomethyl phenyl sulfide 1 and with O-sulfonyloxime 2 were found to proceed with full retention of configuration.

[1]  R. W. Hoffmann,et al.  Concerted and stepwise Grignard additions, probed with a chiral Grignard reagent , 2001 .

[2]  K. Harms,et al.  Asymmetrische Synthese eines chiralen sekundären Grignard-Reagens , 2000 .

[3]  Ricci,et al.  The electrophilic amination of carbanions: an unconventional new entry to C-N bond formation , 2000, Chemistry.

[4]  K. Narasaka,et al.  PREPARATION OF PRIMARY AMINES BY THE ALKYLATION OF O-SULFONYLOXIMES OF BENZOPHENONE DERIVATIVES WITH GRIGNARD REAGENTS , 1999 .

[5]  R. Hoffmann,et al.  α‐Chloralkylmagnesium‐Reagentien mit >90 % ee durch Sulfoxid/Magnesium‐ Austausch , 1999 .

[6]  S. Larsen,et al.  STRUCTURE OF THE RADICALS FORMED IN THE MITSUNOBU REACTION , 1998 .

[7]  I. Beletskaya,et al.  SYNTHESIS OF MONO-, DI-, AND TRISILYL-SUBSTITUTED ALKENES VIA THE HYDROSILYLATION OF METHYLENECYCLOPROPANES CATALYZED BY RH(I) COMPLEXES , 1997 .

[8]  C. Greck,et al.  Electrophilic Amination: New Synthetic Applications , 1997 .

[9]  I. Beletskaya,et al.  Electrochemical activation of nucleophilic substitution in aryl and vinyl halides with [CpFe(CO)(2)](-) anion using homogeneous redox-catalysis , 1996 .

[10]  R. Reamer,et al.  The Effect of Acid Strength on the Mitsunobu Esterification Reaction: Carboxyl vs Hydroxyl Reactivity. , 1996, The Journal of organic chemistry.

[11]  M. Ay,et al.  Electrophilic amination of carbanions , 1989 .

[12]  T. E. Cole,et al.  Chiral synthesis via organoboranes. 8. Synthetic utility of boronic esters of essentially 100% optical purity. Synthesis of primary amines of very high enantiomeric purities , 1986 .

[13]  K. Jönsson,et al.  Cytochrome P-455 nm complex formation in the metabolism of phenylalkylamines. 8. Stereoselectivity in metabolic intermediary complex formation with a series of chiral 2-substituted 1-phenyl-2-aminoethanes. , 1984, Journal of medicinal chemistry.

[14]  B. Trost,et al.  Sulfur activation of azides toward addition of organometallics. Amination of aliphatic carbanions , 1983 .

[15]  N. Yanaihara,et al.  MECHANISMS OF THE REACTIONS OF GRIGNARD REAGENTS. XIII. SINGLE ELECTRON TRANSFER IN THE REDUCTION OF AZOBENZENE AND BENZOPHENONE , 1980 .

[16]  P. J. Gardner,et al.  The relative thermal stabilities of some boron heterocycles , 1964 .

[17]  P. Crowley,et al.  Examination of Synthetic Routes to Monosubstituted Diimides. II. Synthesis of t-Butyl Aryl- and Acylazoformates. Acid-Induced Cleavage of the Thionocarbo-t-butoxy Group1,2 , 1961 .