Scandium‐Catalyzed Asymmetric 1,6‐Addition of 3‐Substituted Oxindoles to Linear Dienyl Ketones

Wang, Zhen; Kang, Tengfei; Yao, Qingzhao; Ji, Jie; Liu, Xiaohua; Lin, Lili; Feng, Xiaoming

doi:10.1002/chem.201500833

Cited by 23 publications

(1 citation statement)

References 67 publications

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“…In conjunction with our study on the development of chiral P -spiro iminophosphorane-catalysed regio-, diastereo- and enantioselective conjugate addition reactions, we herein report a complete inversion of diastereoselectivity in the 1,6-addition333435363738394041424344 of azlactones (oxazol-5(4 H )-ones) to δ-aryl dienyl carbonyl compounds enabled by the slight structural alteration of iminophosphorane catalyst 1 (Fig. 1)374546474849.…”

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confidence: 68%

Complete diastereodivergence in asymmetric 1,6-addition reactions enabled by minimal modification of a chiral catalyst

Uraguchi¹,

Yoshioka²,

Ooi³

2017

Nat Commun

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Catalytic systems that allow selective generation of any diastereomer of a reaction product bearing multiple stereocentres through minimal modification of a single catalyst scaffold remain elusive, particularly for carbon–carbon bond formations requiring simultaneous control of multiple selectivity factors. Here, we report a catalyst-directed pinpoint inversion of diastereochemical preference in the 1,6-addition of azlactones to δ-aryl dienyl carbonyl compounds with full control over other selectivities preserved. This rigorous diastereodivergence is enabled by the slight structural adjustment of a chiral iminophosphorane catalyst, providing access to all the stereoisomers with high regio-, distereo- and enantioselectivity. The utility of this method is demonstrated in the facile stereodivergent preparation of densely functionalized proline derivatives. The experimental and computational elucidation of the origin of the diastereodivergence is also reported.

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confidence: 68%

Complete diastereodivergence in asymmetric 1,6-addition reactions enabled by minimal modification of a chiral catalyst

Uraguchi¹,

Yoshioka²,

Ooi³

2017

Nat Commun

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Addition Reactions: Polar Additions

Knipe¹

2019

Organic Reaction Mechanisms Series

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Regio‐ and Enantioselective Copper‐Catalyzed 1,4‐Conjugate Addition of Trimethylaluminium to Linear α,β,γ,δ‐Unsaturated Alkyl Ketones

Xie

Ling

et al. 2016

Adv Synth Catal

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Ar egio-and enantioselective copper-catalyzed 1,4-conjugate addition of trimethylaluminium to linear d-aryl-substituted a,b,g,d-unsaturated alkyl ketones was developed. As erieso fg,d-unsaturated alkyl ketones were obtained in good yields with high regio-ande nantioselectivity (up to 88% ee and 96:4 dr). Expansion of the reactions cope to substrates containinga romatich eterocycles also afforded good yields ande nantioselectivities( up to 91% ee)w ith very high regioselectivities, exclusivelyp roviding the single 1,4-products.Scheme 2. Expansion of the reaction scopef or aromatic heterocycles.T he reactions of 1o-r (0.200 mmol) with AlMe 3 (1.2 equiv.) were performed at À30 8 8Cf or 12 hi nt he presence of the chiral complex formed in situ from Cu(OAc) 2 ·H 2 O (0.005 mmol, 2.5 mol%) and L6 (0.010 mmol,5 .0 mol%).Scheme 3. Tr ansformations of 2a.

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Scandium‐Catalyzed Asymmetric 1,6‐Addition of 3‐Substituted Oxindoles to Linear Dienyl Ketones

Cited by 23 publications

References 67 publications

Complete diastereodivergence in asymmetric 1,6-addition reactions enabled by minimal modification of a chiral catalyst

Complete diastereodivergence in asymmetric 1,6-addition reactions enabled by minimal modification of a chiral catalyst

Addition Reactions: Polar Additions

Regio‐ and Enantioselective Copper‐Catalyzed 1,4‐Conjugate Addition of Trimethylaluminium to Linear α,β,γ,δ‐Unsaturated Alkyl Ketones

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