Abateact.A four-atop ayntheaia (45 8 total yield) of a mixture of chiral pure Kiaoleucine and Q-alloisoleucine ia reported, via a route compriuing an odic oxidation of suitable acylamide precuraora. Efficient preparations for (~9-2-methylbutylamine from the cheap parent (s)-alcohol are deacribed. Introduction.We have in the paat explored (1) the possibilities to prepare amino acid. from the cotreaponding decarboxylated amines following a four-atop aequence exiating in (i) acylation of the amine t(ii) anodic oxidation of the acylm i n e (ECO)) (iii) nucleophilic substitution of the oxygrouping by the nitrile function using trimethylsilyl cyanide (TI4S-CN)t and (iv) total hydrolyaia (SCEEnE 1).We pceaent here the case whereby a mixture of &-Ile and _p--Ilr is obtained in 45 8 total yield by following this reaction sequence. The starting chiral (S)-2-wthylbutylamine was prepared by aevecal routes from the corresponding chiral, commercially available (s)-alcohol.Organic electrochemical reactions are becoming today popular, the reaaon originating from the high aelectivity that can often be reached in functionalirationa, and the eaay way to achieve many oxidative/raductive transformations with laboratory-friendly devicea (often open and undivided electrochemical cells). Furthermore moat of these reactions are easily upscaled, economically attractive, and clean. The Ross-Bberson-Nyberg methoxylation/acetoxylation of amides (2) is such an example for which aimple Present addresses: 'BOLVAY c Cia, Rue de Ranab-k 310, 8-1120 Brusael .-5 4 5 -how-made instrumentation (1 ) suffices. fuuaaum.varied some paraaeters for the different steps I to 4.In following the reaction path presented in SCBEUE 1, we have first 1: We have considered as protective groupings some that can easily be prepared in good yields, e.g. (i) by formylation (Prot -CBO; reagent ethyl formate), (ii) acetylation (Prot -COCB3; reagent acetic anhydride), (iii) trifluoroacetylation (Prot -COCF3; reagent sodium trifluoroacetamide reacted on 2-methylbutyl broaide), (iv) methyloxycarbonylation (Prot -COOne; Schotten-Baumann with methoxycarbonyl chloride) and (v) tosylamidocarbonylation (Prot -CONRToe; reagent p-tosyl isocyanate). Second best yield. were obtained for the formylderivative (89 t ) , which is the best choice in the subsequent ECO step, while isocyanidation, although proceeding with quantitave conversion, gives an amide that can not be oxidized anodically.

ABSTRACT.10,I2-Dihydroisoindolo[1.2-b]qui~zoline-l2-one (2) waa prepared and fully examined by IH and I3C NMR spectroscopy in CDC13 and DMSO-d6 solution.

Phthalic imidine is shown to be present in DMSO-d6 solution as a 5 : l mixture of 3-amino-1~-isoindol-l-imine (9) and 1,3-diiminoisoindoline (fi) by The amino tautomer 9 also predominates in other solvents: CDC13,

A one s t e p q u a n t i t a t i v e route f o r 5-benzyl-5-methyl hydantoin is obt a i n e d by m e l t i n g a-MePhe with ureum. a t N-3 w i t h c o n s e r v a t i o n of the c h i r a l i t y a t C-5.Diastereomers r e s u l t i n g from asymmetric a l k y l groupings implanted a t N-3 can be s e p a r a t e d by c r y s t a l l i z a t i o n i n aqueous medium. y i e l d s w i t h B a ( 0 H ). T h i s allows t h e p r e p a r a t i o n of e n a n t i o m e r i c pure mines such l i k e 2-methylbutylanine and 2-hydroxypropylamine v i a N-3 a l k y l a t i o n of t h e c h i r a l l y -. t a b l e hydantoin of a-MePhe followed by enantiomeric r e s o l u t i o n and h y d r o l y s i s .