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

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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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",

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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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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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