Highly Diastereo- and Enantioselective Synthesis of α-Spiro-δ-lactams by an Organocascade Reaction

Kaiheng Zhang; Marta Meazza; Vojtěch Dočekal; Mark E. Light; Jan Veselý; Ramon Rios

doi:10.1002/ejoc.201700193

Highly Diastereo- and Enantioselective Synthesis of α-Spiro-δ-lactams by an Organocascade Reaction

Kaiheng Zhang
, Marta Meazza
, Vojtěch Dočekal
, Mark E. Light
, Jan Veselý
, Ramon Rios

Chemistry

University of Southampton
Charles University

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

23 Scopus citations

Abstract

An asymmetric synthesis of α-spiro-δ-lactams by an organocascade reaction of easily accessible starting materials has been accomplished. The catalytic sequence begins with enantioselective Michael addition of a β-ketoamide to an α,β-unsaturated aldehyde, catalyzed by a secondary amine catalyst, and is followed by hemiaminal annulation. Optically enantiopure compounds with three stereogenic centres are obtained in good yields and excellent selectivities (up to >20:1 dr and up to >99 % ee).

Original language	British English
Pages (from-to)	1749-1756
Number of pages	8
Journal	European Journal of Organic Chemistry
Volume	2017
Issue number	13
DOIs	https://doi.org/10.1002/ejoc.201700193
State	Published - 3 Apr 2017

Keywords

Asymmetric synthesis
Enantioselectivity
Michael addition
Organocatalysis
Spirolactams

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title = "Highly Diastereo- and Enantioselective Synthesis of α-Spiro-δ-lactams by an Organocascade Reaction",

abstract = "An asymmetric synthesis of α-spiro-δ-lactams by an organocascade reaction of easily accessible starting materials has been accomplished. The catalytic sequence begins with enantioselective Michael addition of a β-ketoamide to an α,β-unsaturated aldehyde, catalyzed by a secondary amine catalyst, and is followed by hemiaminal annulation. Optically enantiopure compounds with three stereogenic centres are obtained in good yields and excellent selectivities (up to >20:1 dr and up to >99 \% ee).",

keywords = "Asymmetric synthesis, Enantioselectivity, Michael addition, Organocatalysis, Spirolactams",

author = "Kaiheng Zhang and Marta Meazza and Vojt{\v e}ch Do{\v c}ekal and Light, \{Mark E.\} and Jan Vesel{\'y} and Ramon Rios",

note = "Funding Information: K. Z., M. M. and R. R. are grateful for Engineering and Physical Sciences Research Council (EPSRC) Core Capability Funding (EP/K039466/1). V. D. and J. V. gratefully acknowledge financial support from the Charles University Grant Agency (393615). We thank Diamond Light Source for the allocation of beamtime MT8521 on beamline I19. Publisher Copyright: {\textcopyright} 2017 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim",

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doi = "10.1002/ejoc.201700193",

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AU - Zhang, Kaiheng

AU - Meazza, Marta

AU - Dočekal, Vojtěch

AU - Light, Mark E.

AU - Veselý, Jan

AU - Rios, Ramon

N1 - Funding Information: K. Z., M. M. and R. R. are grateful for Engineering and Physical Sciences Research Council (EPSRC) Core Capability Funding (EP/K039466/1). V. D. and J. V. gratefully acknowledge financial support from the Charles University Grant Agency (393615). We thank Diamond Light Source for the allocation of beamtime MT8521 on beamline I19. Publisher Copyright: © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2017/4/3

Y1 - 2017/4/3

N2 - An asymmetric synthesis of α-spiro-δ-lactams by an organocascade reaction of easily accessible starting materials has been accomplished. The catalytic sequence begins with enantioselective Michael addition of a β-ketoamide to an α,β-unsaturated aldehyde, catalyzed by a secondary amine catalyst, and is followed by hemiaminal annulation. Optically enantiopure compounds with three stereogenic centres are obtained in good yields and excellent selectivities (up to >20:1 dr and up to >99 % ee).

AB - An asymmetric synthesis of α-spiro-δ-lactams by an organocascade reaction of easily accessible starting materials has been accomplished. The catalytic sequence begins with enantioselective Michael addition of a β-ketoamide to an α,β-unsaturated aldehyde, catalyzed by a secondary amine catalyst, and is followed by hemiaminal annulation. Optically enantiopure compounds with three stereogenic centres are obtained in good yields and excellent selectivities (up to >20:1 dr and up to >99 % ee).

KW - Asymmetric synthesis

KW - Enantioselectivity

KW - Michael addition

KW - Organocatalysis

KW - Spirolactams

UR - https://www.scopus.com/pages/publications/85017139974

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DO - 10.1002/ejoc.201700193

M3 - Article

AN - SCOPUS:85017139974

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VL - 2017

SP - 1749

EP - 1756

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 13

ER -

Highly Diastereo- and Enantioselective Synthesis of α-Spiro-δ-lactams by an Organocascade Reaction

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Keywords

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