109801-00-5Relevant articles and documents
Synthesis of highly decorated chiral 2-nitro-cyclohexane carboxylic esters through microwave-assisted organocatalyzed cascade reactions
Massolo, Elisabetta,Benaglia, Maurizio,Parravicini, Davide,Brenna, Davide,Annunziata, Rita
, p. 6639 - 6642 (2014)
Starting from (E)-β-substituted-β-nitroacrylates and α,β-unsaturated ketones, a stereoselective organocatalyzed one-pot methodology allowed to synthesize highly decorated chiral 2-nitro-cyclohexane carboxylic esters. The reaction is promoted by Cinchona a
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Petrow,Kaplan
, (1949)
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Evaluation of several fluorinated ATPH derivatives as functionalized Lewis acid receptors for conjugate alkylation to α,β-unsaturated aldehydes with alkyllithium nucleophiles
Ooi, Takashi,Kondo, Yuichiro,Miura, Tomoya,Maruoka, Keiji
, p. 3951 - 3954 (1997)
Several fluorinated aluminum tris(2,6-diphenylphenoxide) (ATPH) derivatives have been synthesized to evaluate, as functionalized Lewis acid receptors, the conjugate alkylation ability to α,β-unsaturated aldehydes by the combined use of alkyllithium nucleo
Accessing Both Retention and Inversion Pathways in Stereospecific, Nickel-Catalyzed Miyaura Borylations of Allylic Pivalates
Zhou, Qi,Srinivas, Harathi D.,Zhang, Songnan,Watson, Mary P.
supporting information, p. 11989 - 11995 (2016/10/07)
We have developed a stereospecific, nickel-catalyzed Miyaura borylation of allylic pivalates, which delivers highly enantioenriched α-stereogenic γ-aryl allylboronates with good yields and regioselectivities. Our complementary sets of conditions enable access to either enantiomer of allylboronate product from a single enantiomer of readily prepared allylic pivalate substrate. Excellent functional group tolerance, yields, regioselectivities, and stereochemical fidelities are observed. The stereochemical switch from stereoretention to stereoinversion largely depends upon solvent and can be explained by competitive pathways for the oxidative addition step. Our mechanistic investigations support a stereoretentive pathway stemming from a directed oxidative addition and a stereoinvertive pathway that is dominant when MeCN blocks coordination of the directing group by binding the nickel catalyst.
1,n-rearrangement of allylic alcohols promoted by hot water: Application to the synthesis of navenone B, a polyene natural product
Li, Pei-Fang,Wang, Heng-Lu,Qu, Jin
, p. 3955 - 3962 (2014/05/20)
It was reported for the first time that hot water as a mildly acidic catalyst efficiently promoted 1,n-rearrangement (n = 3, 5, 7, 9) of allylic alcohols. In some cases, the rearrangement reactions joined isolated C-C double or triple bonds to generate conjugated polyene or enyne structure motifs. We used the 1,3-rearrangement reaction of an allylic alcohol in hot water as part of an attractive new strategy for construction of the polyene natural product navenone B by iterative use of a Grignard reaction, a 1,3-rearrangement of the resulting allylic alcohol, and subsequent oxidation of the rearranged product.
