Synthesis of highly substituted 2-spiropiperidines

TY - JOUR

T1 - Synthesis of highly substituted 2-spiropiperidines

AU - Clarke, Paul Andrew

AU - Griggs, Samuel David

AU - Thompson, Nathan

AU - Fabre, Marie

AU - Tape, Daniel T.

N1 - © The Royal Society of Chemistry 2018. 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 - 2018/9/19

Y1 - 2018/9/19

N2 - 2-Spiropiperidines are a highly desirable, yet under represented structure in drug discovery. 2-Spiropiperidines were synthesised in either a two-pot or one-pot reaction. In the two-pot reaction, the addition of a Weiler dianion to N-Boc imines, followed by deprotection and in situ condensation with a cyclic ketone generated functionalised 2-spiropiperidines in good to excellent yields. In the one-pot reaction, the addition of Chan's diene to N-Boc imines under Maitland-Japp conditions, followed by the addition of sodium bicarbonate and a cyclic ketone formed functionalised 2-spiropiperidines in moderate to good yields.

AB - 2-Spiropiperidines are a highly desirable, yet under represented structure in drug discovery. 2-Spiropiperidines were synthesised in either a two-pot or one-pot reaction. In the two-pot reaction, the addition of a Weiler dianion to N-Boc imines, followed by deprotection and in situ condensation with a cyclic ketone generated functionalised 2-spiropiperidines in good to excellent yields. In the one-pot reaction, the addition of Chan's diene to N-Boc imines under Maitland-Japp conditions, followed by the addition of sodium bicarbonate and a cyclic ketone formed functionalised 2-spiropiperidines in moderate to good yields.

KW - 2-spiropiperidines

KW - medicinal chemistry

UR - http://www.scopus.com/inward/record.url?scp=85053716776&partnerID=8YFLogxK

U2 - 10.1039/C8OB01272E

DO - 10.1039/C8OB01272E

M3 - Article

AN - SCOPUS:85053716776

SN - 1477-0520

VL - 16

SP - 6663

EP - 6674

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 36

ER -