Formal Enantioselective Hydroamination of Non-Activated Alkenes: Transformation of Styrenes into Enantiomerically Pure 1-Phenylethylamines in Chemoenzymatic One-Pot Synthesis

Uthoff F, Sato H, Gröger H (2017)
CHEMCATCHEM 9(4): 555-558.

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Zeitschriftenaufsatz | Veröffentlicht | Englisch
Abstract / Bemerkung
As a complementary approach to current asymmetric synthetic methods, a direct transformation of styrenes into 1-phenylethylamines was developed. The one-pot process represents a formal hydroamination of a non-activated alkene with ammonia and is based on the combination of a Pd/Cu-catalyzed Wacker-oxidation with an enzymatic transamination. A key feature of this process is the compartmentation of the catalytic systems, which turned out to be essential to avoid deactivation of the transaminase by the Cu-component. This one-pot synthesis can be applied to a broad substrate range, which leads to the chiral amines with high conversions and excellent enantioselectivities of >99% ee.
Erscheinungsjahr
Zeitschriftentitel
CHEMCATCHEM
Band
9
Ausgabe
4
Seite(n)
555-558
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Uthoff F, Sato H, Gröger H. Formal Enantioselective Hydroamination of Non-Activated Alkenes: Transformation of Styrenes into Enantiomerically Pure 1-Phenylethylamines in Chemoenzymatic One-Pot Synthesis. CHEMCATCHEM. 2017;9(4):555-558.
Uthoff, F., Sato, H., & Gröger, H. (2017). Formal Enantioselective Hydroamination of Non-Activated Alkenes: Transformation of Styrenes into Enantiomerically Pure 1-Phenylethylamines in Chemoenzymatic One-Pot Synthesis. CHEMCATCHEM, 9(4), 555-558. doi:10.1002/cctc.201601463
Uthoff, F., Sato, H., and Gröger, H. (2017). Formal Enantioselective Hydroamination of Non-Activated Alkenes: Transformation of Styrenes into Enantiomerically Pure 1-Phenylethylamines in Chemoenzymatic One-Pot Synthesis. CHEMCATCHEM 9, 555-558.
Uthoff, F., Sato, H., & Gröger, H., 2017. Formal Enantioselective Hydroamination of Non-Activated Alkenes: Transformation of Styrenes into Enantiomerically Pure 1-Phenylethylamines in Chemoenzymatic One-Pot Synthesis. CHEMCATCHEM, 9(4), p 555-558.
F. Uthoff, H. Sato, and H. Gröger, “Formal Enantioselective Hydroamination of Non-Activated Alkenes: Transformation of Styrenes into Enantiomerically Pure 1-Phenylethylamines in Chemoenzymatic One-Pot Synthesis”, CHEMCATCHEM, vol. 9, 2017, pp. 555-558.
Uthoff, F., Sato, H., Gröger, H.: Formal Enantioselective Hydroamination of Non-Activated Alkenes: Transformation of Styrenes into Enantiomerically Pure 1-Phenylethylamines in Chemoenzymatic One-Pot Synthesis. CHEMCATCHEM. 9, 555-558 (2017).
Uthoff, Florian, Sato, Hirofumi, and Gröger, Harald. “Formal Enantioselective Hydroamination of Non-Activated Alkenes: Transformation of Styrenes into Enantiomerically Pure 1-Phenylethylamines in Chemoenzymatic One-Pot Synthesis”. CHEMCATCHEM 9.4 (2017): 555-558.