Chiral induction from solvents-lactic acid esters in the asymmetric hydroboration of ketones

Stefan H. Hüttenhain; Martin U. Schmidt; Fenja R. Schoepke; Magnus Rueping

doi:10.1016/j.tet.2006.09.111

Chiral induction from solvents-lactic acid esters in the asymmetric hydroboration of ketones

Stefan H. Hüttenhain^*, Martin U. Schmidt, Fenja R. Schoepke, Magnus Rueping

^*Corresponding author for this work

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

7 Scopus citations

Abstract

The hydroboration of acetophenone in the chiral solvent (S)-methyl lactate exhibits moderate enantioselectivities. A six-membered transition state involving the ketone, the borane, and the lactate as the only chiral source is proposed. Molecular modeling explains the experimentally observed enantioselectivities. Calculated ee-values are in accordance with those experimentally observed. Improved ee-values (up to 60%) can be obtained in the presence of stoichiometric amounts of Lewis acid at lower reaction temperatures.

Original language	English (US)
Pages (from-to)	12420-12423
Number of pages	4
Journal	Tetrahedron
Volume	62
Issue number	52
DOIs	https://doi.org/10.1016/j.tet.2006.09.111
State	Published - Dec 25 2006
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Chiral induction from solvents-lactic acid esters in the asymmetric hydroboration of ketones",

abstract = "The hydroboration of acetophenone in the chiral solvent (S)-methyl lactate exhibits moderate enantioselectivities. A six-membered transition state involving the ketone, the borane, and the lactate as the only chiral source is proposed. Molecular modeling explains the experimentally observed enantioselectivities. Calculated ee-values are in accordance with those experimentally observed. Improved ee-values (up to 60%) can be obtained in the presence of stoichiometric amounts of Lewis acid at lower reaction temperatures.",

author = "H{\"u}ttenhain, {Stefan H.} and Schmidt, {Martin U.} and Schoepke, {Fenja R.} and Magnus Rueping",

year = "2006",

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doi = "10.1016/j.tet.2006.09.111",

language = "English (US)",

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T1 - Chiral induction from solvents-lactic acid esters in the asymmetric hydroboration of ketones

AU - Hüttenhain, Stefan H.

AU - Schmidt, Martin U.

AU - Schoepke, Fenja R.

AU - Rueping, Magnus

PY - 2006/12/25

Y1 - 2006/12/25

N2 - The hydroboration of acetophenone in the chiral solvent (S)-methyl lactate exhibits moderate enantioselectivities. A six-membered transition state involving the ketone, the borane, and the lactate as the only chiral source is proposed. Molecular modeling explains the experimentally observed enantioselectivities. Calculated ee-values are in accordance with those experimentally observed. Improved ee-values (up to 60%) can be obtained in the presence of stoichiometric amounts of Lewis acid at lower reaction temperatures.

AB - The hydroboration of acetophenone in the chiral solvent (S)-methyl lactate exhibits moderate enantioselectivities. A six-membered transition state involving the ketone, the borane, and the lactate as the only chiral source is proposed. Molecular modeling explains the experimentally observed enantioselectivities. Calculated ee-values are in accordance with those experimentally observed. Improved ee-values (up to 60%) can be obtained in the presence of stoichiometric amounts of Lewis acid at lower reaction temperatures.

UR - http://www.scopus.com/inward/record.url?scp=33750938158&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2006.09.111

DO - 10.1016/j.tet.2006.09.111

M3 - Article

AN - SCOPUS:33750938158

SN - 0040-4020

VL - 62

SP - 12420

EP - 12423

JO - Tetrahedron

JF - Tetrahedron

IS - 52

ER -

Chiral induction from solvents-lactic acid esters in the asymmetric hydroboration of ketones

Abstract

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