Expanding the scope of the organocatalytic addition of fluorobis(phenylsulfonyl)methane to enals: Enantioselective cascade synthesis of fluoroindane and fluorochromanol derivatives

Young Sug Kim; Sun Min Kim; Bing Wang; Xavier Companyó; Jing Li; Albert Moyano; Seoyoung Im; Zdeněk Tošner; Jung Woon Yang; Ramon Rios

doi:10.1002/adsc.201300703

Expanding the scope of the organocatalytic addition of fluorobis(phenylsulfonyl)methane to enals: Enantioselective cascade synthesis of fluoroindane and fluorochromanol derivatives

Young Sug Kim
, Sun Min Kim
, Bing Wang
, Xavier Companyó
, Jing Li
, Albert Moyano
, Seoyoung Im
, Zdeněk Tošner
, Jung Woon Yang
, Ramon Rios

Chemistry

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

19 Scopus citations

Abstract

Highly enantioselective cascade reactions for the synthesis of fluoroindanes and chromanols derivatives are described. The cascade reactions consisted of either a double Michael reaction or Michael- hemiacetal formation via the addition of fluorobis( phenylsulfonyl)methane (FBSM) to enals. The final products were obtained in good yields with excellent stereoselectivities.

Original language	British English
Pages (from-to)	437-446
Number of pages	10
Journal	Advanced Synthesis and Catalysis
Volume	356
Issue number	2-3
DOIs	https://doi.org/10.1002/adsc.201300703
State	Published - 10 Feb 2014

Keywords

Enantioselectivity
Fluorine
Indanes
Michael reaction
Organocatalysis

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Kim, Y. S., Kim, S. M., Wang, B., Companyó, X., Li, J., Moyano, A., Im, S., Tošner, Z., Yang, J. W., & Rios, R. (2014). Expanding the scope of the organocatalytic addition of fluorobis(phenylsulfonyl)methane to enals: Enantioselective cascade synthesis of fluoroindane and fluorochromanol derivatives. Advanced Synthesis and Catalysis, 356(2-3), 437-446. https://doi.org/10.1002/adsc.201300703

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abstract = "Highly enantioselective cascade reactions for the synthesis of fluoroindanes and chromanols derivatives are described. The cascade reactions consisted of either a double Michael reaction or Michael- hemiacetal formation via the addition of fluorobis( phenylsulfonyl)methane (FBSM) to enals. The final products were obtained in good yields with excellent stereoselectivities.",

keywords = "Enantioselectivity, Fluorine, Indanes, Michael reaction, Organocatalysis",

author = "Kim, \{Young Sug\} and Kim, \{Sun Min\} and Bing Wang and Xavier Company{\'o} and Jing Li and Albert Moyano and Seoyoung Im and Zden{\v e}k To{\v s}ner and Yang, \{Jung Woon\} and Ramon Rios",

year = "2014",

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day = "10",

doi = "10.1002/adsc.201300703",

language = "British English",

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pages = "437--446",

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Kim, YS, Kim, SM, Wang, B, Companyó, X, Li, J, Moyano, A, Im, S, Tošner, Z, Yang, JW & Rios, R 2014, 'Expanding the scope of the organocatalytic addition of fluorobis(phenylsulfonyl)methane to enals: Enantioselective cascade synthesis of fluoroindane and fluorochromanol derivatives', Advanced Synthesis and Catalysis, vol. 356, no. 2-3, pp. 437-446. https://doi.org/10.1002/adsc.201300703

Expanding the scope of the organocatalytic addition of fluorobis(phenylsulfonyl)methane to enals: Enantioselective cascade synthesis of fluoroindane and fluorochromanol derivatives. / Kim, Young Sug; Kim, Sun Min; Wang, Bing et al.
In: Advanced Synthesis and Catalysis, Vol. 356, No. 2-3, 10.02.2014, p. 437-446.

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

TY - JOUR

T1 - Expanding the scope of the organocatalytic addition of fluorobis(phenylsulfonyl)methane to enals

T2 - Enantioselective cascade synthesis of fluoroindane and fluorochromanol derivatives

AU - Kim, Young Sug

AU - Kim, Sun Min

AU - Wang, Bing

AU - Companyó, Xavier

AU - Li, Jing

AU - Moyano, Albert

AU - Im, Seoyoung

AU - Tošner, Zdeněk

AU - Yang, Jung Woon

AU - Rios, Ramon

PY - 2014/2/10

Y1 - 2014/2/10

N2 - Highly enantioselective cascade reactions for the synthesis of fluoroindanes and chromanols derivatives are described. The cascade reactions consisted of either a double Michael reaction or Michael- hemiacetal formation via the addition of fluorobis( phenylsulfonyl)methane (FBSM) to enals. The final products were obtained in good yields with excellent stereoselectivities.

AB - Highly enantioselective cascade reactions for the synthesis of fluoroindanes and chromanols derivatives are described. The cascade reactions consisted of either a double Michael reaction or Michael- hemiacetal formation via the addition of fluorobis( phenylsulfonyl)methane (FBSM) to enals. The final products were obtained in good yields with excellent stereoselectivities.

KW - Enantioselectivity

KW - Fluorine

KW - Indanes

KW - Michael reaction

KW - Organocatalysis

UR - https://www.scopus.com/pages/publications/84899936342

U2 - 10.1002/adsc.201300703

DO - 10.1002/adsc.201300703

M3 - Article

AN - SCOPUS:84899936342

SN - 1615-4150

VL - 356

SP - 437

EP - 446

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 2-3

ER -

Expanding the scope of the organocatalytic addition of fluorobis(phenylsulfonyl)methane to enals: Enantioselective cascade synthesis of fluoroindane and fluorochromanol derivatives

Abstract

Keywords

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