1999
DOI: 10.1055/s-1999-2756
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Efficient 1,3-Asymmetric Inductions during Nucleophilic Additions to Imine and Iminium Ion Derivatives

Abstract: Two new b-amino alcohols have been synthesized by a reaction between an organolithium compound 1 involving an allylsilane moiety with either an imine or an oxazolidine derived from (S)-phenylglycinol. These reactions occurred in good yields and with high diastereoselectivity. Both amino-alcohols were engaged in cyclization reaction with glyoxal to afford in two steps highly functionalized bicyclic lactones.Key words: organolithium reagent, asymmetric synthesis, b-amino alcoholsThe addition of organometallic re… Show more

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Cited by 16 publications
(4 citation statements)
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“…[41] The additions of {2-[(trimethylsilyl)methyl]prop-2-enyl}lithium to (S)-phenylglycinol-derived oxazolidines (90) also afforded β-amino alcohols 91 with high diastereoselectivities (Scheme 29). [42] Scheme 29 Probably because of a slow tautomeric equilibration process, an open (A) and two C-2-epimeric cyclic (B and C) tautomers of the condensation product 92 derived from (R)-phenylglycinol and 2,2,2-trifluoroacetophenone could be isolated. When compounds 92AϪC were treated with various organolithium reagents, N-substituted amino alcohol derivatives 93 or 94 were obtained with moderate to excellent diastereoselectivities.…”
Section: Applicationsmentioning
confidence: 99%
“…[41] The additions of {2-[(trimethylsilyl)methyl]prop-2-enyl}lithium to (S)-phenylglycinol-derived oxazolidines (90) also afforded β-amino alcohols 91 with high diastereoselectivities (Scheme 29). [42] Scheme 29 Probably because of a slow tautomeric equilibration process, an open (A) and two C-2-epimeric cyclic (B and C) tautomers of the condensation product 92 derived from (R)-phenylglycinol and 2,2,2-trifluoroacetophenone could be isolated. When compounds 92AϪC were treated with various organolithium reagents, N-substituted amino alcohol derivatives 93 or 94 were obtained with moderate to excellent diastereoselectivities.…”
Section: Applicationsmentioning
confidence: 99%
“…1,3-Oxazolidines are remarkably versatile molecules having found use as chiral auxiliaries, , as intermediates for more complex chiral heterocycles, and as prodrugs for improving the pharmacokinetic profile of certain β -amino alcohol pharmacophores . They are ideally suited as scaffolds for combinatorial library generation because they have a rigid core that possesses four sites for the incorporation of diversity elements and can be synthesized with a high degree of chiral integrity (Figure A).…”
Section: Introductionmentioning
confidence: 99%
“…Pioneering works in this field have been concerned with the diastereoselective addition of alkyl or aryllithium reagents onto oxazolidines derived from amino alcohol and especially from phenylglycinol. As part of a program aimed at emphasizing the efficiency of asymmetric syntheses of pipecolic acid derivatives from functionalized β-amino alcohols, we have recently explored the reactions between unsaturated organolithium reagents and oxazolidines 1 .…”
mentioning
confidence: 99%