Influence of N-protecting groups on the stereochemical course of [4+2] cycloaddition of activated dienes to α-amino aldehydes
Asymmetric synthesis of 6-substituted-5,6-dihydro-2-methoxy-2H-pyrans (3) and 2-substituted-2,3-dihydropyran-4-ones (6) via (4+2) cycloaddition.
References (31)
- et al.
Tetrahedron
(1987) - et al.
Tetrahedron
(1987) - et al.
Tetrahedron Lett.
(1988) - et al.
Tetrahedron Lett.
(1988) - et al.
Heterocycles
(1986) - et al.
J. Chem. Soc.
(1989) - et al.
J. Org. Chem.
(1986) - et al.
J. Am. Chem. Soc.
(1989) - et al.
J. Org. Chem.
(1982) - et al.
Chem. Rev.
(1989)
J. Org. Chem.
Synthesis
J. Am. Chem. Soc.
Angew. Chem. Int. Ed. Engl.
Heterocycles
Cited by (16)
Advances in serinals for asymmetric synthesis
2013, TetrahedronCitation Excerpt :The cross-metathesis reactions of anti-215a with alkenylated substances A (7-nitro-4-benzofurazanamine-(NBD)) and B–D (boron-dipyrromethene (BDP) analogues) followed by treatment with HCl in dioxane offered the final BODIPY-labelled sphingosines 216a–d, respectively (Scheme 54). By applying a similar methodology, Bandhuvula et al.72 also synthesized BODIPY-labelled sphingosine 1-phosphate substrates 217a and 217b as sphingosine 1-phosphate (S1P) lyase (SPL) by an olefin cross-metathesis reaction between alkenylated compounds A (BODIPY analogue) and B (4-benzofurazanamine-(NBD)) with an N-protected allylic alcohol derived from Garner's aldehyde (S-1a) (Scheme 55) in a similar reaction to that discussed in Scheme 54. For biological evaluation of γ-aminophosphonates 220C–F and 221 as potent, subtype-selective sphingosine 1-phosphate receptor agonists and antagonists, Foss et al. carried out73 Horner–Wadsworth–Emmons olefination of S-1a with bis-phosphonate (A) and fluorinated bis-phosphonate (B), resulting in the olefins 218A,B, which after reduction, simultaneous acetonide deprotection and Jones' oxidation offered the protected amino acids (R)-219A,B in 40 and 18% yield, respectively.
Diastereoselective addition of vinylmagnesium halides to variously N-mono- and N,N-diprotected L-alaninals
1997, Tetrahedron AsymmetryThe synthesis of carbohydrate derivatives from acyclic precursors
1993, TetrahedronRecent Advances in Inverse-Electron-Demand Hetero-Diels–Alder Reactions of 1-Oxa-1,3-Butadienes
2016, Topics in Current Chemistry