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- W2207601869 abstract "A general synthesis of highly substituted pyrrolizidines can be performed by a multicomponent 1,3-dipolar cycloaddition using proline ester hydrochlorides, aldehydes and dipolarophiles, at room temperature without catalysts or in the presence of AgOAc (5 mol %). In the case of (2S,4R)-4-hydroxyproline derivatives it is possible to obtain enantioenriched pyrrolizidines with high control of the regio- and diastereoselectivity affording the adducts 2,4-trans-2,5-trans according to an endo-approach and a S-dipole geometry of the in situ generated azomethine ylide. For proline esters a similar regioselectivity and endo-diastereoselectivity are observed when the dipole promotes an α-attack. However, when ethyl glyoxylate is used as aldehyde component the γ-attack of the S-ylide takes place preferentially giving rise the opposite regioselectivity for acrylic dipolarophiles, being crucial the role of silver acetate. In this case, the exo-adducts with a 2,3-cis-2,5-trans relative configuration are diastereoselectively obtained. In addition, computational studies have also been carried out to shed light on the origins of the diastereo- and regioselectivity observed for the described 1,3-dipolar cycloadditions." @default.
- W2207601869 created "2016-06-24" @default.
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- W2207601869 date "2015-12-01" @default.
- W2207601869 modified "2023-09-27" @default.
- W2207601869 title "Regio and diastereoselective multicomponent 1,3-dipolar cycloadditions between prolinate hydrochlorides, aldehydes and dipolarophiles for the direct synthesis of pyrrolizidines" @default.
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- W2207601869 cites W1739982854 @default.
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- W2207601869 cites W1967008717 @default.
- W2207601869 cites W1969148272 @default.
- W2207601869 cites W1970765539 @default.
- W2207601869 cites W1973523910 @default.
- W2207601869 cites W1973953671 @default.
- W2207601869 cites W1981911740 @default.
- W2207601869 cites W1985820982 @default.
- W2207601869 cites W1986473729 @default.
- W2207601869 cites W1991145838 @default.
- W2207601869 cites W1995878805 @default.
- W2207601869 cites W1998490900 @default.
- W2207601869 cites W2000317223 @default.
- W2207601869 cites W2003703614 @default.
- W2207601869 cites W2009994114 @default.
- W2207601869 cites W2016477351 @default.
- W2207601869 cites W2024384845 @default.
- W2207601869 cites W2026558443 @default.
- W2207601869 cites W2028374102 @default.
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- W2207601869 cites W2085336624 @default.
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- W2207601869 cites W2296967601 @default.
- W2207601869 cites W2323635073 @default.
- W2207601869 cites W2328938511 @default.
- W2207601869 cites W2333946260 @default.
- W2207601869 cites W2334467335 @default.
- W2207601869 cites W2335266174 @default.
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- W2207601869 cites W2951886030 @default.
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- W2207601869 doi "https://doi.org/10.1016/j.tet.2015.10.064" @default.
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