A Two-Step Synthesis of 2-Spiropiperidines

TY - JOUR

T1 - A Two-Step Synthesis of 2-Spiropiperidines

AU - Griggs, Samuel D.

AU - Thompson, Nathan

AU - Tape, Daniel T.

AU - Fabre, Marie

AU - Clarke, Paul A.

N1 - © 2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details

PY - 2017/7/12

Y1 - 2017/7/12

N2 - A general two-step synthesis of 2-spiropiperidines has been developed. δ-Amino-β-ketoesters can be reacted with cyclic ketones to generate 2-spiropiperidines in good to excellent yields. The 2-spiropiperidines formed occupy an under-explored region of 3D-chemical space and are novel scaffolds for use in drug discovery programs. These 2-spiropiperidines can be further functionalised to generate small highly sp3-rich structures, which exhibit an excellent likeness to lead-molecules in drug discovery.

AB - A general two-step synthesis of 2-spiropiperidines has been developed. δ-Amino-β-ketoesters can be reacted with cyclic ketones to generate 2-spiropiperidines in good to excellent yields. The 2-spiropiperidines formed occupy an under-explored region of 3D-chemical space and are novel scaffolds for use in drug discovery programs. These 2-spiropiperidines can be further functionalised to generate small highly sp3-rich structures, which exhibit an excellent likeness to lead-molecules in drug discovery.

KW - Maitland–Japp

KW - medicinal chemistry

KW - piperidine

KW - scaffolds

KW - spirocyclic

UR - http://www.scopus.com/inward/record.url?scp=85021278492&partnerID=8YFLogxK

U2 - 10.1002/chem.201702467

DO - 10.1002/chem.201702467

M3 - Article

AN - SCOPUS:85021278492

SN - 0947-6539

VL - 23

SP - 9262

EP - 9265

JO - Chemistry : A European Journal

JF - Chemistry : A European Journal

IS - 39

ER -