Synthesis of two (S)-indoline-based chiral auxiliaries and their use in diastereoselective alkylation reactions
Ansvarig organisation
2006 (Engelska)Ingår i: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 17, nr 13, s. 1952-1957Artikel i tidskrift (Refereegranskat) Published
Abstract [en]
Two chiral auxiliaries, 2-[(S)-indolin-2-yl]propan-2-ol 1a and (S)-2-(2-methoxypropan-2-yl)indoline 1b, were synthesised from enantiomerically pure (S)-indoline-2-carboxylic acid 3. High diastereoselectivities in alkylations of enolates of the propanoylamides derived from the two auxiliaries are presented. Surprisingly, both auxiliaries induced the same selectivity at the newly created stereogenic centre. The benzyl bromide and n-butyl iodide alkylation reactions showed diastereomeric ratios that were moderate (81:19) to very good (96:4) and with very good yields (86-98%). When LiCl was used as an enolate coordinating agent, in the benzylation of the enolate from propanoylated auxiliary 1a, a very high crude diastereomeric ratio was obtained (99.7:0.3).
Ort, förlag, år, upplaga, sidor
2006. Vol. 17, nr 13, s. 1952-1957
Nyckelord [en]
Synthesis chiral auxiliaries diastereoselective alkylation reactions
Nationell ämneskategori
Kemi
Identifikatorer
URN: urn:nbn:se:miun:diva-3876DOI: 10.1016/j.tetasy.2006.07.002ISI: 000240242300005Scopus ID: 2-s2.0-33746979728Lokalt ID: 4196OAI: oai:DiVA.org:miun-3876DiVA, id: diva2:28908
2008-09-302008-09-302017-12-12Bibliografiskt granskad