ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Studies towards the synthesis of a chiral primary α-phosphinoalkanamine 1a are reported. O-Activated. N-carbamate-protected phenylalaninol 3a did not undergo SN reaction with KPPh2: instead, after N-deprotonation, intramolecular substitution led to formation of the aziridine derivative 5a (Scheme 2). N-Phthalimido-protected, O-activated phenylalaninol 3b also underwent an intramolecular process on treatment with KPPh2, i.e., an unusual aryl-acyliminium cyclization furnishing the (epoxymethano)isoindolo[1,2-a]isoquinolinone 7 (Scheme 3). In a reaction with KPPh2, the N,N-dibenzyl-protected and activated phenylalaninol 3d finally yielded the intermolecular SN reaction product 2a (Scheme 4). However, debenzylation by catalytic hydrogenation turned out to be impossible.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19980810506
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