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Highly diastereo and enantioselective synthesis of α-spiro-δ-lactams via organocascade reaction

Highly diastereo and enantioselective synthesis of α-spiro-δ-lactams via organocascade reaction
Highly diastereo and enantioselective synthesis of α-spiro-δ-lactams via organocascade reaction
An asymmetric synthesis of α-spiro-δ-lactam via organocascade reaction from easily accessible starting materials is reported. The catalytic sequence undergoes enantioselective Michael addition of β-ketoamide to α,β-unsaturated aldehyde catalysed by a secondary amine catalyst, followed by hemiaminal annulation. Optically enantiopure compounds with two contiguous stereogenic centres are obtained in good yields and excellent selectivities (up to >20:1 dr and up to >99% ee).
1434-193X
1749-1756
Zhang, Kaiheng
60fdb96c-3613-47c2-aeb7-6a6366f4ab67
Meazza, Marta
c4665645-8c77-4cfd-aa02-6bcc3341c1aa
Vojtech, Docekal
4ff6b1aa-0af0-4fe3-a41e-d2499344c17a
Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Veselý, Jan
9d4ecc53-859e-451a-a018-636d416bb3fe
Rios Torres, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Zhang, Kaiheng
60fdb96c-3613-47c2-aeb7-6a6366f4ab67
Meazza, Marta
c4665645-8c77-4cfd-aa02-6bcc3341c1aa
Vojtech, Docekal
4ff6b1aa-0af0-4fe3-a41e-d2499344c17a
Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Veselý, Jan
9d4ecc53-859e-451a-a018-636d416bb3fe
Rios Torres, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441

Zhang, Kaiheng, Meazza, Marta, Vojtech, Docekal, Light, Mark, Veselý, Jan and Rios Torres, Ramon (2017) Highly diastereo and enantioselective synthesis of α-spiro-δ-lactams via organocascade reaction. European Journal of Organic Chemistry, 2017 (13), 1749-1756. (doi:10.1002/ejoc.201700193).

Record type: Article

Abstract

An asymmetric synthesis of α-spiro-δ-lactam via organocascade reaction from easily accessible starting materials is reported. The catalytic sequence undergoes enantioselective Michael addition of β-ketoamide to α,β-unsaturated aldehyde catalysed by a secondary amine catalyst, followed by hemiaminal annulation. Optically enantiopure compounds with two contiguous stereogenic centres are obtained in good yields and excellent selectivities (up to >20:1 dr and up to >99% ee).

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ejoc201700193 - Accepted Manuscript
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Accepted/In Press date: 9 February 2017
e-pub ahead of print date: 9 February 2017
Published date: 3 April 2017
Organisations: Characterisation and Analytics, Chemistry, Organic Chemistry: SCF

Identifiers

Local EPrints ID: 406452
URI: http://eprints.soton.ac.uk/id/eprint/406452
ISSN: 1434-193X
PURE UUID: 9ad4592b-a74e-4775-b88e-b3698560a99e
ORCID for Marta Meazza: ORCID iD orcid.org/0000-0003-4382-0626
ORCID for Mark Light: ORCID iD orcid.org/0000-0002-0585-0843
ORCID for Ramon Rios Torres: ORCID iD orcid.org/0000-0002-3843-8521

Catalogue record

Date deposited: 10 Mar 2017 10:47
Last modified: 08 Oct 2020 04:25

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