Synthesis and stereoselective evaluation of a (1R)-(–)-myrtenal-derived pseudo C2-symmetric dodecaheterocycle as a potential heterofunctional chiral auxiliary

Anahí C. Sánchez-Chávez; Ma Elena Vargas-Díaz; Julio C. Ontiveros-Rodríguez; Salvador Pérez-Estrada; Gustavo G. Flores-Bernal; Daniel Mendoza-Espinosa; Alejandro Álvarez-Hernández; Francisco Delgado; Joaquín Tamariz; L. Gerardo Zepeda-Vallejo

doi:10.1016/j.tetlet.2018.11.012

Synthesis and stereoselective evaluation of a (1R)-(–)-myrtenal-derived pseudo C₂-symmetric dodecaheterocycle as a potential heterofunctional chiral auxiliary

Anahí C. Sánchez-Chávez, Ma Elena Vargas-Díaz, Julio C. Ontiveros-Rodríguez, Salvador Pérez-Estrada, Gustavo G. Flores-Bernal, Daniel Mendoza-Espinosa, Alejandro Álvarez-Hernández, Francisco Delgado, Joaquín Tamariz, L. Gerardo Zepeda-Vallejo

Escuela Nacional de Ciencias Biológicas (ENCB)

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2 Scopus citations

Abstract

The synthesis and diastereoselective performance of the pseudo C₂-symmetric dodecaheterocycle 3 in nucleophilic and electrophilic reactions are reported. Compound 3 proved to be a highly diastereoselective template to generate a pair of enantiomeric moieties within its structure in a programmed manner. Hence, this study describes the synthesis of a novel potential heterobifunctional chiral auxiliary.

Original language	English
Pages (from-to)	4437-4441
Number of pages	5
Journal	Tetrahedron Letters
Volume	59
Issue number	50
DOIs	https://doi.org/10.1016/j.tetlet.2018.11.012
State	Published - 12 Dec 2018

Keywords

Bis-sulfoxide
Diastereoselectivity
Electrophilic addition
Myrtenal
Nucleophilic addition

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10.1016/j.tetlet.2018.11.012

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Sánchez-Chávez, A. C., Elena Vargas-Díaz, M., Ontiveros-Rodríguez, J. C., Pérez-Estrada, S., Flores-Bernal, G. G., Mendoza-Espinosa, D., Álvarez-Hernández, A., Delgado, F., Tamariz, J., & Gerardo Zepeda-Vallejo, L. (2018). Synthesis and stereoselective evaluation of a (1R)-(–)-myrtenal-derived pseudo C₂-symmetric dodecaheterocycle as a potential heterofunctional chiral auxiliary. Tetrahedron Letters, 59(50), 4437-4441. https://doi.org/10.1016/j.tetlet.2018.11.012

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title = "Synthesis and stereoselective evaluation of a (1R)-(–)-myrtenal-derived pseudo C2-symmetric dodecaheterocycle as a potential heterofunctional chiral auxiliary",

abstract = "The synthesis and diastereoselective performance of the pseudo C2-symmetric dodecaheterocycle 3 in nucleophilic and electrophilic reactions are reported. Compound 3 proved to be a highly diastereoselective template to generate a pair of enantiomeric moieties within its structure in a programmed manner. Hence, this study describes the synthesis of a novel potential heterobifunctional chiral auxiliary.",

keywords = "Bis-sulfoxide, Diastereoselectivity, Electrophilic addition, Myrtenal, Nucleophilic addition",

author = "S{\'a}nchez-Ch{\'a}vez, {Anah{\'i} C.} and {Elena Vargas-D{\'i}az}, Ma and Ontiveros-Rodr{\'i}guez, {Julio C.} and Salvador P{\'e}rez-Estrada and Flores-Bernal, {Gustavo G.} and Daniel Mendoza-Espinosa and Alejandro {\'A}lvarez-Hern{\'a}ndez and Francisco Delgado and Joaqu{\'i}n Tamariz and {Gerardo Zepeda-Vallejo}, L.",

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year = "2018",

month = dec,

day = "12",

doi = "10.1016/j.tetlet.2018.11.012",

language = "Ingl{\'e}s",

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Sánchez-Chávez, AC, Elena Vargas-Díaz, M, Ontiveros-Rodríguez, JC, Pérez-Estrada, S, Flores-Bernal, GG, Mendoza-Espinosa, D, Álvarez-Hernández, A, Delgado, F , Tamariz, J & Gerardo Zepeda-Vallejo, L 2018, 'Synthesis and stereoselective evaluation of a (1R)-(–)-myrtenal-derived pseudo C₂-symmetric dodecaheterocycle as a potential heterofunctional chiral auxiliary', Tetrahedron Letters, vol. 59, no. 50, pp. 4437-4441. https://doi.org/10.1016/j.tetlet.2018.11.012

Synthesis and stereoselective evaluation of a (1R)-(–)-myrtenal-derived pseudo C₂-symmetric dodecaheterocycle as a potential heterofunctional chiral auxiliary. / Sánchez-Chávez, Anahí C.; Elena Vargas-Díaz, Ma; Ontiveros-Rodríguez, Julio C. et al.
In: Tetrahedron Letters, Vol. 59, No. 50, 12.12.2018, p. 4437-4441.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Synthesis and stereoselective evaluation of a (1R)-(–)-myrtenal-derived pseudo C2-symmetric dodecaheterocycle as a potential heterofunctional chiral auxiliary

AU - Sánchez-Chávez, Anahí C.

AU - Elena Vargas-Díaz, Ma

AU - Ontiveros-Rodríguez, Julio C.

AU - Pérez-Estrada, Salvador

AU - Flores-Bernal, Gustavo G.

AU - Mendoza-Espinosa, Daniel

AU - Álvarez-Hernández, Alejandro

AU - Delgado, Francisco

AU - Tamariz, Joaquín

AU - Gerardo Zepeda-Vallejo, L.

PY - 2018/12/12

Y1 - 2018/12/12

N2 - The synthesis and diastereoselective performance of the pseudo C2-symmetric dodecaheterocycle 3 in nucleophilic and electrophilic reactions are reported. Compound 3 proved to be a highly diastereoselective template to generate a pair of enantiomeric moieties within its structure in a programmed manner. Hence, this study describes the synthesis of a novel potential heterobifunctional chiral auxiliary.

AB - The synthesis and diastereoselective performance of the pseudo C2-symmetric dodecaheterocycle 3 in nucleophilic and electrophilic reactions are reported. Compound 3 proved to be a highly diastereoselective template to generate a pair of enantiomeric moieties within its structure in a programmed manner. Hence, this study describes the synthesis of a novel potential heterobifunctional chiral auxiliary.

KW - Bis-sulfoxide

KW - Diastereoselectivity

KW - Electrophilic addition

KW - Myrtenal

KW - Nucleophilic addition

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U2 - 10.1016/j.tetlet.2018.11.012

DO - 10.1016/j.tetlet.2018.11.012

M3 - Artículo

SN - 0040-4039

VL - 59

SP - 4437

EP - 4441

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 50

ER -

Sánchez-Chávez AC, Elena Vargas-Díaz M, Ontiveros-Rodríguez JC, Pérez-Estrada S, Flores-Bernal GG, Mendoza-Espinosa D et al. Synthesis and stereoselective evaluation of a (1R)-(–)-myrtenal-derived pseudo C₂-symmetric dodecaheterocycle as a potential heterofunctional chiral auxiliary. Tetrahedron Letters. 2018 Dec 12;59(50):4437-4441. doi: 10.1016/j.tetlet.2018.11.012

Synthesis and stereoselective evaluation of a (1R)-(–)-myrtenal-derived pseudo C₂-symmetric dodecaheterocycle as a potential heterofunctional chiral auxiliary

Abstract

Keywords

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