THE USE OF ALPHA-HETEROATOM SUBSTITUTED C-NUCLEOPHILES AND HETEROCUMULENES IN ENANTIOSELECTIVE AND DIASTEREOSELECTIVE SYNTHESES

Authors
DOLLING W HELLRUNG B SIEBEL HM
Citation
W. Dolling et al., THE USE OF ALPHA-HETEROATOM SUBSTITUTED C-NUCLEOPHILES AND HETEROCUMULENES IN ENANTIOSELECTIVE AND DIASTEREOSELECTIVE SYNTHESES, Phosphorus, sulfur and silicon and the related elements, 95-6(1-4), 1994, pp. 409-411
Citations number
5
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Phosphorus, sulfur and silicon and the related elements → ACNP
ISSN journal
10426507
Volume
95-6
Issue
1-4
Year of publication
1994
Pages
409 - 411
Database
ISI
SICI code
1042-6507(1994)95-6:1-4<409:TUOASC>2.0.ZU;2-Y
Abstract
C-Nucleophiles derived by deprotonation from tropinone 1, cis-bicyclo[ 3.3.0]octane-3,7-dione 3, and its 1,5-dimethyl derivative 4, react wit h carbon disulfide and alkylating agents to the corresponding racemate s of their 2-[bis(alkylthio)-methylene] derivatives 2, 5, and 6, respe ctively. Diastereoselective alkylations of alkyl )-2-methoxymethyl-pyr rolidine-1-dithiocarboxylates 7 and its (8) isomers 8 were studied. Th e enantiomeric dithiocarbamates 7 and 8 react in a diastereoselective manner with alkyl halides after deprotonation with LiTMP/LiBr at -78 d egrees C in THF to 9.