Lewis Base Assisted Brønsted Base Catalysis: Direct Asymmetric Allylic Alkylation of Indenes

Cui, Hai‐Lei; Sun, Xun-Hao; Jiang, Lin; Dong, Lin; Chen, Ying‐Chun

doi:10.1002/ejoc.201101255

Cited by 14 publications

(4 citation statements)

References 51 publications

(9 reference statements)

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“…It was proposed that the Si-face of the activated MBH adduct was blocked by the bulky substituent of the catalyst, thus favouring the attack from its Re-face by the corresponding indenide (Scheme 14). 22 Recently, more research groups have engaged in this active field. The Shibata 23 and Tan groups 24 independently reported the use of bis(phenylsulfonyl)methane 33a (X = H) in the allylic alkylation with MBH carbonates 2.…”

Section: Allylic Alkylations With Modified Mbh Adducts 21 Early Historymentioning

confidence: 99%

Organocatalytic asymmetric transformations of modified Morita–Baylis–Hillman adducts

2012

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Chiral Lewis basic tertiary amines or phosphines can enable properly modified Morita-Baylis-Hillman (MBH) adducts to undergo asymmetric allylic substitutions with a wide range of nucleophiles. In addition, assisted by a Brønsted base, chiral Lewis bases can also catalytically convert modified MBH adducts into allylic ylides, which can be engaged in a variety of asymmetric annulation reactions. This tutorial review will focus on such chiral Lewis base-catalysed asymmetric transformations of MBH adducts, especially those developed over the past five years, allowing for the rapid construction of densely functionalised chiral molecules with high levels of regio- and stereoselectivities.

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Section: Allylic Alkylations With Modified Mbh Adducts 21 Early Historymentioning

confidence: 99%

Organocatalytic asymmetric transformations of modified Morita–Baylis–Hillman adducts

2012

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“…[119] A different procedure for the synthesis of comparable butenolides was reported by Shi et al [120] The same group was also able to apply substituted indenes for alkylations of MBH carbonates in 1,2-dichloroethane as solvent catalyzed by (DHQD) 2 AQN 119. [121] Whereas Cheng et al obtained very good results with the same catalyst in reactions of benzofuranones (Scheme 56). This procedure is also suitable for the construction of quaternary carbon centers.…”

Section: Allylic Alkylations Of Mbh Productsmentioning

confidence: 99%

“…The same group was also able to apply substituted indenes for alkylations of MBH carbonates in 1,2‐dichloroethane as solvent catalyzed by (DHQD) 2 AQN 119 121. Whereas Cheng et al.…”

Section: Allylic Alkylations Of Mbh Productsmentioning

confidence: 99%

Recent Advances in Organocatalytic Methods for Asymmetric CC Bond Formation

Scheffler

Mahrwald

2013

Chemistry A European J

197

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Beyond a doubt organocatalysis belongs to the most exciting and innovative chapters of organic chemistry today. Organocatalysis has emerged not only as a complement to metal-catalyzed reactions and to biocatalysis over the last decade, but also provides new asymmetric organocatalyzed reactions that cannot be accomplished by metal- or biocatalyzed reactions so far. A large number of organocatalytic processes are already well established in organic synthesis. Nevertheless, the number of publications in this field is still on the increase; new important results are produced constantly. This review gives a detailed overview of the latest developments and main streams in organocatalyzed asymmetric CC bond formation processes of the last three years. It is intended to outline the most important current findings focused on especially new synthetic methodologies.

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“…Recently, Lewis base-catalyzed asymmetric allylic substitutions of MBH adducts have become an alternative and viable option for accessing various chiral C -, N -, O -, P -, and S -, allylic and spirocyclic compounds. We have also demonstrated that modified Cinchona alkaloids are effective catalysts for the asymmetric allylic alkylation of bis(phenylsulfonyl)methane (BSM), fluoro-bis(phenylsulfonyl)methane (FBSM) and allylic hydroxylation using water with MBH carbonates.…”

Section: Introductionmentioning

confidence: 99%

Direct Asymmetric Allylic Alkenylation of N-Itaconimides with Morita–Baylis–Hillman Carbonates

Yang

Tan

et al. 2012

J. Org. Chem.

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The asymmetric allylic alkenylation of Morita-Baylis-Hillman (MBH) carbonates with N-itaconimides as nucleophiles has been developed using a commercially available Cinchona alkaloid catalyst. A variety of multifunctional chiral α-methylene-β-maleimide esters were attained in moderate to excellent yields (up to 99%) and good to excellent enantioselectivities (up to 91% ee). The origin of the regio- and stereoselectivity was verified by DFT methods. Calculated geometries and relative energies of various transition states strongly support the observed regio- and enantioselectivity.

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Lewis Base Assisted Brønsted Base Catalysis: Direct Asymmetric Allylic Alkylation of Indenes

Abstract: A direct, asymmetric allylic alkylation of indenes with Morita-Baylis-Hillman (MBH) carbonates has been developed based on a Lewis base assisted Brønsted base catalysis strategy. This process is promoted by a modified cinchona alkaloid hydroquinidine (anthraquinone-1,4-diyl) diether

Cited by 14 publications

References 51 publications

Organocatalytic asymmetric transformations of modified Morita–Baylis–Hillman adducts

Organocatalytic asymmetric transformations of modified Morita–Baylis–Hillman adducts

Recent Advances in Organocatalytic Methods for Asymmetric CC Bond Formation

Direct Asymmetric Allylic Alkenylation of N-Itaconimides with Morita–Baylis–Hillman Carbonates

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