A short and efficient formal synthesis of (R)-pipecolic acid from the ring expansion of chiral aziridine

被引：0

作者：

Pareek, Archana ^{[1
]}

Khom, Sonam Tashi ^{[1
]}

Saikia, Pranjit ^{[1
]}

Yadav, Nagendra Nath ^{[1
]}

机构：

[1] North Eastern Reg Inst Sci & Technol NERIST, Dept Chem, Nirjuli 791109, Arunachal Prade, India

来源：

MONATSHEFTE FUR CHEMIE | 2024年 / 155卷 / 05期

关键词：

Chiral aziridines; Ring strain; Bicyclic aziridinium ion; Ring expansion; Pipecolic acid; ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; PIPERIDINE ALKALOIDS; CONCISE; NUCLEOPHILES; REACTIVITY; RESOLUTION; EPOXIDES;

D O I：

10.1007/s00706-024-03187-3

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Ring expansion of 4-[(2R)-1-[(1R)-1-phenylethyl]aziridin-2-yl]butyl tosylate obtained from tosylation of 4-[(2R)-1-[(1R)-1-phenylethyl]aziridin-2-yl]butan-1-ol via formation of 1-azabicyclo[4.1.0]heptane tosylate gives substituted piperidine. The ring openings of azabicycloheptane tosylate with acetate nucleophiles proceeded in highly regio- and stereoselective manner with release of the ring-strain of the three-membered aziridine ring through the breakage of either C-N bond. This ring expansion streategy of aziridine provides a short route for asymmetric synthesis of biologically active natural alkaloid such as (R)-pipecolic acid.

引用

页码：525 / 529

页数：5

共 50 条

[1] A short and efficient formal synthesis of (R)-pipecolic acid from the ring expansion of chiral aziridine
Archana Pareek
Sonam Tashi Khom
Pranjit Saikia
Nagendra Nath Yadav
Monatshefte für Chemie - Chemical Monthly, 2024, 155 : 525 - 529
[2] Efficient Organocatalytic Chiral Synthesis of (R)-Pipecolic Acid
Panchgalle, Sharad P.
More, Vijaykumar S.
Khanvilkar, Mahesh B.
EGYPTIAN JOURNAL OF CHEMISTRY, 2022, 65 (13): : 1441 - 1446
[3] A formal synthesis of (-)-swainsonine from a chiral aziridine
Choi, Hwan Geun
Kwon, Ji Hye
Kim, Jong Chan
Lee, Won Koo
Eum, Heesung
Ha, Hyun-Joon
TETRAHEDRON LETTERS, 2010, 51 (25) : 3284 - 3285
[4] A short enantioselective total synthesis of (R)- and (S)-pipecolic acid
Chavan, Subhash P.
Khairnar, Lalit B.
Chavan, Prakash N.
Kalbhor, Dinesh B.
TETRAHEDRON-ASYMMETRY, 2014, 25 (16-17) : 1246 - 1251
[5] Chiral aziridine ring opening: facile synthesis of (R)-modletine and (R)-phenoxybenzamine hydrochloride
Viswanadh, N.
Velayudham, R.
Jambu, S.
Sasikumar, M.
Muthukrishnan, M.
TETRAHEDRON LETTERS, 2015, 56 (38) : 5269 - 5271
[6] Aziridine ring-containing chiral ligands as highly efficient catalysts in asymmetric synthesis
Rachwalski, Michal
Jarzynski, Szymon
Legniak, Stanislaw
TETRAHEDRON-ASYMMETRY, 2013, 24 (07) : 421 - 425
[7] A short enantioselective synthesis of pipecolic acid
FernandezGarcia, C
McKervey, MA
TETRAHEDRON-ASYMMETRY, 1995, 6 (12) : 2905 - 2906
[8] Enantioselective syntheses of (R)-pipecolic acid, (2R,3R)-3-hydroxypipecolic acid, β-(+)-conhydrine and (-)-swainsonine using an aziridine derived common chiral synthon
Chavan, Subhash P.
Khairnar, Lalit B.
Pawar, Kailash P.
Chavan, Prakash N.
Kawale, Sanket A.
RSC ADVANCES, 2015, 5 (62): : 50580 - 50590
[9] Highly stereoselective directed reactions and an efficient synthesis of azafuranoses from a chiral aziridine
Lee, Hogyu
Kim, Jun Hee
Lee, Won Koo
Cho, Jaeheung
Nam, Wonwoo
Lee, Jaedeok
Ha, Hyun-Joon
ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (22) : 3629 - 3634
[10] An efficient, asymmetric synthesis of pipecolic acid and 2-alkyl pipecolic acids
Hou, DR
Hung, SY
Hu, CC
TETRAHEDRON-ASYMMETRY, 2005, 16 (23) : 3858 - 3864

← 1 2 3 4 5 →