Palladium-Catalyzed Asymmetric (3 + 2) Cycloaddition of Vinyl Epoxides with Substituted Propiolates. Enantioselective Formation of 2,3,4-Trisubstituted 2,3-Dihydrofurans.
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DOI: 10.1021/acs.orglett.2c00253
Abstract: Alkynyl esters are viable dipolarophiles for the palladium-catalyzed asymmetric (3 + 2) cycloaddition with vinyl epoxides. The chiral dihydrofurans are obtained in high yields and high ee values. The use of a chiral benzylic substituted… read more here.
Keywords: asymmetric cycloaddition; vinyl epoxides; cycloaddition vinyl; palladium catalyzed ... See more keywords
Access to Chiral Tetrahydroquinazolines/1,3-Benzoxazines via Iridium-Catalyzed Asymmetric [4 + 2] Cycloaddition.
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DOI: 10.1021/acs.orglett.3c01004
Abstract: An iridium-catalyzed asymmetric [4 + 2] cycloaddition of 1,3,5-triazinanes with 2-(1-hydroxyallyl)anilines/2-(1-hydroxyallyl)phenols has been developed, providing a straightforward and efficient approach to a wide range of tetrahydroquinazolines in good yields and excellent enantioselectivities (up to >99%… read more here.
Keywords: asymmetric cycloaddition; catalyzed asymmetric; iridium catalyzed; access chiral ... See more keywords
Design of an Organocatalytic Asymmetric (4 + 3) Cycloaddition of 2-Indolylalcohols with Dienolsilanes
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DOI: 10.1021/jacs.2c02216
Abstract: Here we present the design of a highly enantioselective, catalytic (4 + 3) cycloaddition of gem-dialkyl 2-indolyl alcohols and dienolsilanes, enabled by strong and confined IDPi Lewis acids. The method furnishes novel bicyclo[3.2.2]cyclohepta[b]indoles with up… read more here.
Keywords: asymmetric cycloaddition; organocatalytic asymmetric; design; design organocatalytic ... See more keywords
PC-Phos Enabled Catalytic Palladium-heteroallyl Asymmetric Cycloaddition.
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DOI: 10.1021/jacs.2c09799
Abstract: Asymmetric cycloaddition reactions are the most powerful tool to the expeditious construction of enantioenriched cyclic motifs in organic chemistry. In sharp contrast to well-developed cycloaddition reactions via the palladium-trimethylenemethane (Pd-TMM) intermediate, hetero (3 + 2)… read more here.
Keywords: palladium heteroallyl; asymmetric cycloaddition; phos; cycloaddition ... See more keywords
Asymmetric [3+2] cycloaddition of 3-amino oxindole-based azomethine ylides with α,β-ynones: a straightforward approach to spirooxindoles incorporating 2,5-dihydropyrroles and pyrroles.
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DOI: 10.1039/c7cc01653k
Abstract: An organocatalytic asymmetric [3+2] cycloaddition of 3-amino oxindole-based azomethine ylides and α,β-ynones has been developed. This reaction afforded spiro[dihydropyrrole-2,3'-oxindole] products in high chemical yields with excellent stereoselectivities (up to 99% yields, >20 : 1 dr and >99%… read more here.
Keywords: based azomethine; oxindole based; amino oxindole; cycloaddition amino ... See more keywords
Catalytic asymmetric [4 + 1] cycloaddition to synthesize chiral pyrazoline-spirooxindoles
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DOI: 10.1039/d3qo00320e
Abstract: An asymmetric formal [4 + 1] cycloaddition of N-unprotected oxindole 3-pyridinium salts and α-halo hydrazones to access chiral pyrazoline-spirooxindoles is realized by using a chiral N,N’-dioxide-Pr(OTf)3 complex as catalyst. The... read more here.
Keywords: asymmetric cycloaddition; catalytic asymmetric; pyrazoline spirooxindoles; chiral pyrazoline ... See more keywords