Abstract
The highly diastereoselective oxy-Michael addition of the "naked" anion of (6S)-methyl δ lactol to alkylidiene-, arylidene-, and heteroarylidene-malonate derivatives leading to the direct formation of THP*-protected β-hydroxy ester derivatives is described. Subsequent acid-mediated deprotection affords the enantioenriched aldol products in quantitative yields.
Original language | English |
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Pages (from-to) | 1357-1360 |
Number of pages | 3 |
Journal | Organic Letters |
Volume | 6 |
Issue number | 9 |
DOIs | |
Publication status | Published - 29 Apr 2004 |
Keywords
- Crystal structure; Molecular structure (of (methyltetrahydropyranyloxy)hydroxymethyl(methyl)pentanol); Asymmetric synthesis and induction (stereoselective prepn. of (methyltetrahydropyranyloxy)alkanoates via stereoselective Michael addn. of methyltetrahydropyranol to alkylidene- or arylidenemalonates); Michael reaction (stereoselective; stereoselective prepn. of (methyltetrahydropyranyloxy)alkanoates via stereoselective Michael addn. of methyltetrahydropyranol to alkylidene- or arylidenemalonates); Esters Role: RCT (Reactant), RACT (Reactant or reagent) (a,b-unsatd.; stereoselective prepn. of (methyltetrahydropyranyloxy)alkanoates via stereoselective Michael addn. of methyltetrahydropyranol to alkylidene- or arylidenemalonates)
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CCDC 239111: Experimental Crystal Structure Determination
Buchanan, D. J. (Contributor), Dixon, D. (Contributor) & Hernandez-Juan, F. A. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2004
DOI: 10.5517/cc80t8b, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc80t8b&sid=DataCite
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