Chirally modified n-butyllithium: Tuning the composition, structure, and enantioselectivity with modular fencholates

Mark J.M. Vlaar; Andreas W. Ehlers; Frans J.J. De Kanter; Marius Schakel; Anthony L. Spek; Martin Lutz; Nadejda Sigal; Yitzhak Apeloig; Koop Lammertsma

doi:10.1002/1521-3773(20001117)39:22<4133::AID-ANIE4133>3.0.CO;2-X

Chirally modified n-butyllithium: Tuning the composition, structure, and enantioselectivity with modular fencholates

Mark J.M. Vlaar
, Andreas W. Ehlers
, Frans J.J. De Kanter
, Marius Schakel
, Anthony L. Spek
, Martin Lutz
, Nadejda Sigal
, Yitzhak Apeloig
, Koop Lammertsma

Vrije Universiteit Amsterdam
Utrecht University
Technion-Israel Institute of Technology

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

42 Citations (Scopus)

Abstract

2:2 instead of 3:1 is the ratio between the lithium anisylfencholate 1 and the nBuLi units in the aggregate formed from these components (see structure) when the substituent is changed from X = H to X = SiMe₃. DFT calculations confirm the different stability sequences of the 2:2 and 3:1 aggregates with the two different X substituents. The 2:2 aggregate gives a higher enantioselectivity (80% ee) than the 3:1 aggregate in the nBuLi addition to benzaldehyde.

Original language	English
Pages (from-to)	4133-4136
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	39
Issue number	22
DOIs	https://doi.org/10.1002/1521-3773(20001117)39:22<4133::AID-ANIE4133>3.0.CO;2-X
Publication status	Published - 17 Nov 2000
Externally published	Yes

Keywords

Carbanions
Chirality
Density functional calculations
Enantioselectivity
Lithium

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/1521-3773(20001117)39:22<4133::AID-ANIE4133>3.0.CO;2-X

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Vlaar, M. J. M., Ehlers, A. W., De Kanter, F. J. J., Schakel, M., Spek, A. L., Lutz, M., Sigal, N., Apeloig, Y., & Lammertsma, K. (2000). Chirally modified n-butyllithium: Tuning the composition, structure, and enantioselectivity with modular fencholates. Angewandte Chemie - International Edition, 39(22), 4133-4136. https://doi.org/10.1002/1521-3773(20001117)39:22<4133::AID-ANIE4133>3.0.CO;2-X

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title = "Chirally modified n-butyllithium: Tuning the composition, structure, and enantioselectivity with modular fencholates",

abstract = "2:2 instead of 3:1 is the ratio between the lithium anisylfencholate 1 and the nBuLi units in the aggregate formed from these components (see structure) when the substituent is changed from X = H to X = SiMe3. DFT calculations confirm the different stability sequences of the 2:2 and 3:1 aggregates with the two different X substituents. The 2:2 aggregate gives a higher enantioselectivity (80\% ee) than the 3:1 aggregate in the nBuLi addition to benzaldehyde.",

keywords = "Carbanions, Chirality, Density functional calculations, Enantioselectivity, Lithium",

author = "Vlaar, \{Mark J.M.\} and Ehlers, \{Andreas W.\} and \{De Kanter\}, \{Frans J.J.\} and Marius Schakel and Spek, \{Anthony L.\} and Martin Lutz and Nadejda Sigal and Yitzhak Apeloig and Koop Lammertsma",

year = "2000",

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doi = "10.1002/1521-3773(20001117)39:22<4133::AID-ANIE4133>3.0.CO;2-X",

language = "English",

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Vlaar, MJM, Ehlers, AW, De Kanter, FJJ, Schakel, M, Spek, AL, Lutz, M, Sigal, N, Apeloig, Y & Lammertsma, K 2000, 'Chirally modified n-butyllithium: Tuning the composition, structure, and enantioselectivity with modular fencholates', Angewandte Chemie - International Edition, vol. 39, no. 22, pp. 4133-4136. https://doi.org/10.1002/1521-3773(20001117)39:22<4133::AID-ANIE4133>3.0.CO;2-X

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T1 - Chirally modified n-butyllithium

T2 - Tuning the composition, structure, and enantioselectivity with modular fencholates

AU - Vlaar, Mark J.M.

AU - Ehlers, Andreas W.

AU - De Kanter, Frans J.J.

AU - Schakel, Marius

AU - Spek, Anthony L.

AU - Lutz, Martin

AU - Sigal, Nadejda

AU - Apeloig, Yitzhak

AU - Lammertsma, Koop

PY - 2000/11/17

Y1 - 2000/11/17

N2 - 2:2 instead of 3:1 is the ratio between the lithium anisylfencholate 1 and the nBuLi units in the aggregate formed from these components (see structure) when the substituent is changed from X = H to X = SiMe3. DFT calculations confirm the different stability sequences of the 2:2 and 3:1 aggregates with the two different X substituents. The 2:2 aggregate gives a higher enantioselectivity (80% ee) than the 3:1 aggregate in the nBuLi addition to benzaldehyde.

AB - 2:2 instead of 3:1 is the ratio between the lithium anisylfencholate 1 and the nBuLi units in the aggregate formed from these components (see structure) when the substituent is changed from X = H to X = SiMe3. DFT calculations confirm the different stability sequences of the 2:2 and 3:1 aggregates with the two different X substituents. The 2:2 aggregate gives a higher enantioselectivity (80% ee) than the 3:1 aggregate in the nBuLi addition to benzaldehyde.

KW - Carbanions

KW - Chirality

KW - Density functional calculations

KW - Enantioselectivity

KW - Lithium

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M3 - Article

AN - SCOPUS:0034680550

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JF - Angewandte Chemie - International Edition

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ER -

Chirally modified n-butyllithium: Tuning the composition, structure, and enantioselectivity with modular fencholates

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Keywords

ASJC Scopus subject areas

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