Tuning the peri effect for enantioselectivity: Asymmetric hydrogenation of unfunctionalized olefins with the BIPI ligands

Carl A. Busacca; Bo Qu; Nicole Grět; Keith R. Fandrick; Anjan K. Saha; Maurice Marsini; Diana Reeves; Nizar Haddad; Magnus Eriksson; Jiang Ping Wu; Nelu Grinberg; Heewon Lee; Zhibin Li; Bruce Lu; Dajun Chen; Yaping Hong; Shengli Ma; Chris H. Senanayake

doi:10.1002/adsc.201201104

Tuning the peri effect for enantioselectivity: Asymmetric hydrogenation of unfunctionalized olefins with the BIPI ligands

Carl A. Busacca, Bo Qu, Nicole Grět, Keith R. Fandrick, Anjan K. Saha, Maurice Marsini, Diana Reeves, Nizar Haddad, Magnus Eriksson, Jiang Ping Wu, Nelu Grinberg, Heewon Lee, Zhibin Li, Bruce Lu, Dajun Chen, Yaping Hong, Shengli Ma, Chris H. Senanayake

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

29 Scopus citations

Abstract

The modular nature of the BIPI ligands allows for systematic optimization of each ligand region. The development of ligands optimized for asymmetric hydrogenation of the challenging unfunctionalized olefin substrate class is described. The naphthyl peri position, C-8, has been identified as a critical stereocontrol element in the design of these ligands. Highly enantioselective ligands suitable for hydrogenation of tri- and tetrasubstituted olefins are detailed.

Original language	English (US)
Pages (from-to)	1455-1463
Number of pages	9
Journal	Advanced Synthesis and Catalysis
Volume	355
Issue number	8
DOIs	https://doi.org/10.1002/adsc.201201104
State	Published - May 17 2013
Externally published	Yes

Keywords

BIPI ligands
asymmetric hydrogenation
naphthalenes
peri position
unfunctionalized olefins

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.201201104

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Busacca, C. A., Qu, B., Grět, N., Fandrick, K. R., Saha, A. K., Marsini, M., Reeves, D., Haddad, N., Eriksson, M., Wu, J. P., Grinberg, N., Lee, H., Li, Z., Lu, B., Chen, D., Hong, Y., Ma, S., & Senanayake, C. H. (2013). Tuning the peri effect for enantioselectivity: Asymmetric hydrogenation of unfunctionalized olefins with the BIPI ligands. Advanced Synthesis and Catalysis, 355(8), 1455-1463. https://doi.org/10.1002/adsc.201201104

Busacca, CA, Qu, B, Grět, N, Fandrick, KR, Saha, AK, Marsini, M, Reeves, D, Haddad, N, Eriksson, M, Wu, JP, Grinberg, N, Lee, H, Li, Z, Lu, B, Chen, D, Hong, Y, Ma, S & Senanayake, CH 2013, 'Tuning the peri effect for enantioselectivity: Asymmetric hydrogenation of unfunctionalized olefins with the BIPI ligands', Advanced Synthesis and Catalysis, vol. 355, no. 8, pp. 1455-1463. https://doi.org/10.1002/adsc.201201104

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abstract = "The modular nature of the BIPI ligands allows for systematic optimization of each ligand region. The development of ligands optimized for asymmetric hydrogenation of the challenging unfunctionalized olefin substrate class is described. The naphthyl peri position, C-8, has been identified as a critical stereocontrol element in the design of these ligands. Highly enantioselective ligands suitable for hydrogenation of tri- and tetrasubstituted olefins are detailed.",

keywords = "BIPI ligands, asymmetric hydrogenation, naphthalenes, peri position, unfunctionalized olefins",

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doi = "10.1002/adsc.201201104",

language = "English (US)",

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AU - Busacca, Carl A.

AU - Qu, Bo

AU - Grět, Nicole

AU - Fandrick, Keith R.

AU - Saha, Anjan K.

AU - Marsini, Maurice

AU - Reeves, Diana

AU - Haddad, Nizar

AU - Eriksson, Magnus

AU - Wu, Jiang Ping

AU - Grinberg, Nelu

AU - Lee, Heewon

AU - Li, Zhibin

AU - Lu, Bruce

AU - Chen, Dajun

AU - Hong, Yaping

AU - Ma, Shengli

AU - Senanayake, Chris H.

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AB - The modular nature of the BIPI ligands allows for systematic optimization of each ligand region. The development of ligands optimized for asymmetric hydrogenation of the challenging unfunctionalized olefin substrate class is described. The naphthyl peri position, C-8, has been identified as a critical stereocontrol element in the design of these ligands. Highly enantioselective ligands suitable for hydrogenation of tri- and tetrasubstituted olefins are detailed.

KW - BIPI ligands

KW - asymmetric hydrogenation

KW - naphthalenes

KW - peri position

KW - unfunctionalized olefins

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Tuning the peri effect for enantioselectivity: Asymmetric hydrogenation of unfunctionalized olefins with the BIPI ligands

Abstract

Keywords

ASJC Scopus subject areas

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