Stereospecific Rearrangements during the Synthesis of Pyrrolidines and Related Heterocycles from Cyclizations of Amino Alcohols with Vinyl Sulfones

Journal of Organic Chemistry

Volumn 68, Issue 24, 2003, Pages 9389-9393

  Back, Thomas G ^a   Parvez, Masood ^a   Zhai, Huimin ^a  

^a UNIVERSITY OF CALGARY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

STEREOSPECIFIC REARRANGEMENT;

ALKYLATION; AMINO ACIDS; AROMATIC COMPOUNDS; CHLORINATION; ISOMERIZATION; NEGATIVE IONS; STEREOCHEMISTRY;

ALCOHOLS;

2 (2 PIPERIDINE)ETHANOL; 2 (PIPERIDINE)METHANOL; 3 (BENZENESULFONYL) N BENZYL 4 METHYLPYRROLIDINE; ALCOHOL DERIVATIVE; ALPHA AMINO ACID; AMINOALCOHOL; AZIRIDINE DERIVATIVE; INDOLIZIDINE DERIVATIVE; METHANOL DERIVATIVE; METHYL GROUP; PHENYL GROUP; PYRROLIDINE DERIVATIVE; QUINOLIZIDINE DERIVATIVE; SULFONE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ADDITION REACTION; ALKYLATION; ARTICLE; CHEMICAL REACTION; CHLORINATION; CONJUGATE; CYCLIZATION; ELIMINATION REACTION; ISOMERISM; STEREOSPECIFICITY; TRANS ISOMER;

ALKYLATION; AMINO ALCOHOLS; CYCLIZATION; HETEROCYCLIC COMPOUNDS; MODELS, CHEMICAL; PYRROLIDINES; STEREOISOMERISM; SULFONES; VINYL COMPOUNDS;

EID: 0345686449     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0350864     Document Type: Article

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37. We note that the additions of amines 11a and 11b to 1b provided yields of only 29% and 26% of the rearranged adducts 22a and 22b, even after 3 and 4 days, respectively, in refluxing xylenes. Extensive decomposition of the amine starting materials was observed during this time, along with the gradual appearance of 1c and 1d. On the other hand, the direct addition of 2a to 1b was considerably more facile and proceeded even in the lower boiling solvent 2-propanol to afford 50% of 19 after refluxing for only 1 day. When refluxed in xylenes, the reaction was largely complete in less than 1 day and proceeded cleanly to form 19 in 91% yield after 2 days.