Enantioselective desymmetrization via carbonyl-directed catalytic asymmetric hydroboration and Suzuki-Miyaura cross-coupling

Gia L. Hoang; Zhao Di Yang; Sean M. Smith; Rhitankar Pal; Judy L. Miska; Damaris E. Pérez; Libbie S.W. Pelter; Xiao Cheng Zeng; James M. Takacs

doi:10.1021/ol503764d

Enantioselective desymmetrization via carbonyl-directed catalytic asymmetric hydroboration and Suzuki-Miyaura cross-coupling

Gia L. Hoang, Zhao Di Yang, Sean M. Smith, Rhitankar Pal, Judy L. Miska, Damaris E. Pérez, Libbie S.W. Pelter, Xiao Cheng Zeng, James M. Takacs

Chemistry

Research output: Contribution to journal › Article

24 Scopus citations

Abstract

The rhodium-catalyzed enantioselective desymmetrization of symmetric γ,δ-unsaturated amides via carbonyl-directed catalytic asymmetric hydroboration (directed CAHB) affords chiral secondary organoboronates with up to 98% ee. The chiral γ-borylated products undergo palladium-catalyzed Suzuki-Miyaura cross-coupling via the trifluoroborate salt with stereoretention.

Original language	English (US)
Pages (from-to)	940-943
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	4
DOIs	https://doi.org/10.1021/ol503764d
State	Published - Feb 20 2015

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/ol503764d

Fingerprint Dive into the research topics of 'Enantioselective desymmetrization via carbonyl-directed catalytic asymmetric hydroboration and Suzuki-Miyaura cross-coupling'. Together they form a unique fingerprint.

Cite this

Hoang, G. L., Yang, Z. D., Smith, S. M., Pal, R., Miska, J. L., Pérez, D. E., Pelter, L. S. W., Zeng, X. C., & Takacs, J. M. (2015). Enantioselective desymmetrization via carbonyl-directed catalytic asymmetric hydroboration and Suzuki-Miyaura cross-coupling. Organic Letters, 17(4), 940-943. https://doi.org/10.1021/ol503764d

Enantioselective desymmetrization via carbonyl-directed catalytic asymmetric hydroboration and Suzuki-Miyaura cross-coupling. / Hoang, Gia L.; Yang, Zhao Di; Smith, Sean M.; Pal, Rhitankar; Miska, Judy L.; Pérez, Damaris E.; Pelter, Libbie S.W.; Zeng, Xiao Cheng ; Takacs, James M.

In: Organic Letters, Vol. 17, No. 4, 20.02.2015, p. 940-943.

Research output: Contribution to journal › Article

@article{83cfa463ed4848368ca8d2f1a776e930,

title = "Enantioselective desymmetrization via carbonyl-directed catalytic asymmetric hydroboration and Suzuki-Miyaura cross-coupling",

abstract = "The rhodium-catalyzed enantioselective desymmetrization of symmetric γ,δ-unsaturated amides via carbonyl-directed catalytic asymmetric hydroboration (directed CAHB) affords chiral secondary organoboronates with up to 98% ee. The chiral γ-borylated products undergo palladium-catalyzed Suzuki-Miyaura cross-coupling via the trifluoroborate salt with stereoretention.",

author = "Hoang, {Gia L.} and Yang, {Zhao Di} and Smith, {Sean M.} and Rhitankar Pal and Miska, {Judy L.} and P{\'e}rez, {Damaris E.} and Pelter, {Libbie S.W.} and Zeng, {Xiao Cheng} and Takacs, {James M.}",

year = "2015",

month = feb,

day = "20",

doi = "10.1021/ol503764d",

language = "English (US)",

volume = "17",

pages = "940--943",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "4",

}

TY - JOUR

T1 - Enantioselective desymmetrization via carbonyl-directed catalytic asymmetric hydroboration and Suzuki-Miyaura cross-coupling

AU - Hoang, Gia L.

AU - Yang, Zhao Di

AU - Smith, Sean M.

AU - Pal, Rhitankar

AU - Miska, Judy L.

AU - Pérez, Damaris E.

AU - Pelter, Libbie S.W.

AU - Zeng, Xiao Cheng

AU - Takacs, James M.

PY - 2015/2/20

Y1 - 2015/2/20

N2 - The rhodium-catalyzed enantioselective desymmetrization of symmetric γ,δ-unsaturated amides via carbonyl-directed catalytic asymmetric hydroboration (directed CAHB) affords chiral secondary organoboronates with up to 98% ee. The chiral γ-borylated products undergo palladium-catalyzed Suzuki-Miyaura cross-coupling via the trifluoroborate salt with stereoretention.

AB - The rhodium-catalyzed enantioselective desymmetrization of symmetric γ,δ-unsaturated amides via carbonyl-directed catalytic asymmetric hydroboration (directed CAHB) affords chiral secondary organoboronates with up to 98% ee. The chiral γ-borylated products undergo palladium-catalyzed Suzuki-Miyaura cross-coupling via the trifluoroborate salt with stereoretention.

UR - http://www.scopus.com/inward/record.url?scp=84923339093&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84923339093&partnerID=8YFLogxK

U2 - 10.1021/ol503764d

DO - 10.1021/ol503764d

M3 - Article

C2 - 25642639

AN - SCOPUS:84923339093

VL - 17

SP - 940

EP - 943

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 4

ER -