Asymmetric Reduction of Lactam-based β-Aminoacrylates. Synthesis of Heterocyclic β2-Amino Acids

Hugo Rego Campello; Jeremy S. Parker; Matthew W D Perry; Per Ryberg; Timothy Gallagher

doi:10.1021/acs.orglett.6b02074

Asymmetric Reduction of Lactam-based β-Aminoacrylates. Synthesis of Heterocyclic β2-Amino Acids

Hugo Rego Campello, Jeremy S. Parker, Matthew W D Perry, Per Ryberg, Timothy Gallagher

Research output: Contribution to journal › Article (Academic Journal) › peer-review

19 Citations (Scopus)

488 Downloads (Pure)

Abstract

The ability to affect asymmetric reduction of heterocyclic β-aminoacrylates 1 (n = 1–3) has been assessed with pyrrolidine and piperidone variants generating the corresponding N-heterocyclic β2-amino acids 3b and 5b with high enantioselectivity (≥97% ee) using a Rh/WALPHOS catalyst combination. The use of the carboxylic acid substrate was essential; the corresponding esters do undergo reduction but led to racemic products. The seven-ring azepanone variant (as the carboxylic acid 9b) underwent reduction, but only a minimal level of asymmetric induction was observed.

Original language	English
Pages (from-to)	4124–4127
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	16
Early online date	10 Aug 2016
DOIs	https://doi.org/10.1021/acs.orglett.6b02074
Publication status	Published - 19 Aug 2016

Keywords

Asymmetric reduction

Access to Document

10.1021/acs.orglett.6b02074

Full-text PDF (accepted author manuscript)
This is the author accepted manuscript (AAM). The final published version (version of record) is available online via ACS at http://pubs.acs.org/doi/full/10.1021/acs.orglett.6b02074#Abstract. Please refer to any applicable terms of use of the publisher.
Accepted author manuscript, 533 KBLicence: CC BY-NC

Handle.net

Persistent link

Emeritus Professor Timothy Gallagher
- T.Gallagherbristol.acuk
- School of Chemistry - Emeritus Professor
- Elizabeth Blackwell Institute for Health Research
- Bristol Neuroscience
Person: Member, Honorary and Visiting Academic

Cite this

@article{4efa0b39517541c0bebffdd3ca7316c2,

title = "Asymmetric Reduction of Lactam-based β-Aminoacrylates. Synthesis of Heterocyclic β2-Amino Acids",

abstract = "The ability to affect asymmetric reduction of heterocyclic β-aminoacrylates 1 (n = 1–3) has been assessed with pyrrolidine and piperidone variants generating the corresponding N-heterocyclic β2-amino acids 3b and 5b with high enantioselectivity (≥97\% ee) using a Rh/WALPHOS catalyst combination. The use of the carboxylic acid substrate was essential; the corresponding esters do undergo reduction but led to racemic products. The seven-ring azepanone variant (as the carboxylic acid 9b) underwent reduction, but only a minimal level of asymmetric induction was observed.",

keywords = "Asymmetric reduction",

author = "\{Rego Campello\}, Hugo and Parker, \{Jeremy S.\} and Perry, \{Matthew W D\} and Per Ryberg and Timothy Gallagher",

year = "2016",

month = aug,

day = "19",

doi = "10.1021/acs.orglett.6b02074",

language = "English",

volume = "18",

pages = "4124–4127",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "16",

}

TY - JOUR

T1 - Asymmetric Reduction of Lactam-based β-Aminoacrylates. Synthesis of Heterocyclic β2-Amino Acids

AU - Rego Campello, Hugo

AU - Parker, Jeremy S.

AU - Perry, Matthew W D

AU - Ryberg, Per

AU - Gallagher, Timothy

PY - 2016/8/19

Y1 - 2016/8/19

N2 - The ability to affect asymmetric reduction of heterocyclic β-aminoacrylates 1 (n = 1–3) has been assessed with pyrrolidine and piperidone variants generating the corresponding N-heterocyclic β2-amino acids 3b and 5b with high enantioselectivity (≥97% ee) using a Rh/WALPHOS catalyst combination. The use of the carboxylic acid substrate was essential; the corresponding esters do undergo reduction but led to racemic products. The seven-ring azepanone variant (as the carboxylic acid 9b) underwent reduction, but only a minimal level of asymmetric induction was observed.

AB - The ability to affect asymmetric reduction of heterocyclic β-aminoacrylates 1 (n = 1–3) has been assessed with pyrrolidine and piperidone variants generating the corresponding N-heterocyclic β2-amino acids 3b and 5b with high enantioselectivity (≥97% ee) using a Rh/WALPHOS catalyst combination. The use of the carboxylic acid substrate was essential; the corresponding esters do undergo reduction but led to racemic products. The seven-ring azepanone variant (as the carboxylic acid 9b) underwent reduction, but only a minimal level of asymmetric induction was observed.

KW - Asymmetric reduction

U2 - 10.1021/acs.orglett.6b02074

DO - 10.1021/acs.orglett.6b02074

M3 - Article (Academic Journal)

C2 - 27508307

SN - 1523-7060

VL - 18

SP - 4124

EP - 4127

JO - Organic Letters

JF - Organic Letters

IS - 16

ER -

Asymmetric Reduction of Lactam-based β-Aminoacrylates. Synthesis of Heterocyclic β2-Amino Acids

Abstract

Keywords

Access to Document

Handle.net

Fingerprint

Profiles

Emeritus Professor Timothy Gallagher

Cite this