The asymmetric synthesis of α-amino acids via the addition of grignard reagents to imine derivatives

DOI: 10.1016/S0040-4020(01)90125-5

Source and publish data:

Tetrahedron p. 5163 - 5178 (1992)

Update date:2022-07-29

Topics:

Authors:

Hamon, David P. G.

Massy-Westropp, Ralph A.

Razzino, Pasquale

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1016/S0040-4020(01)90125-5

The ester-8-phenylmenthyl N-Boc-glycinate 5a, undergoes free radical bromination by N-bromosuccinimide to give 8-phenylmenthyl N-Boc-bromoglycinate 8. Treatment of the bromide 8 with a variety of Grignard reagents at low temperature gave 8-phenylmenthyl (S-N-Boc-2-alkylgrycinates with high diastereoselectivity. Conditions were found for the hydrolysis of these derivatives with no racemization of the resultant amino acid.

Full text of DOI:10.1016/S0040-4020(01)90125-5

Products guided by the article

Product name:(1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl (R)-2-<(tert-butoxycarbonyl)amino>pentanoate

Cas No:145308-95-8

R&D Labs maybe for 145308-95-8

Deltachem(QingDao)Co.,Ltd.

Contact:+8618766299236

Address:ROOM808, BUILDING2,NO.230 SHEN ZHEN ROAD, LAOSHAN DISTRICT
SOGA ENTERPRISES ASIA GROUP

Contact:+86-633-8332928

Address:No.1,Huanghai Yilu.Rizhao,Shandong
jiangsu haian chemical co.,ltd.

Contact:86-513-15851283853

Address:No.99,Changjiang West Road,Haian County,Jiangsu Province,China
Hangzhou Haichem Co.,Ltd.

Contact:+86-571-86025531 / 86024803

Address:1218-24 Guangyin Mansion,42 Fengqi East Road
He Bei Shun Er Chemical Co., LTD.

Contact:86-0311-86996932/86860168

Address:No 18,North street

Relevant to this article

Pharmacophore and docking-based hierarchical virtual screening for the designing of aldose reductase inhibitors: Synthesis and biological evaluation

Doi:10.1007/s00044-016-1510-5
(2016)
A family of novel bifunctional organocatalysts: Highly enantioselective alcoholysis of meso cyclic anhydrides and its application for synthesis of the key intermediate of P2X₇ receptor antagonists

Doi:10.1016/j.cclet.2013.04.009
(2013)
Ligand-controlled remarkable regio- and stereodivergence in intermolecular hydrosilylation of internal alkynes: Experimental and theoretical studies

Doi:10.1021/ja405752w
(2013)
Synthesis of chiral β-amino acid derivatives by asymmetric hydrosilylation with an imidazole derived organocatalyst

Doi:10.1016/j.tet.2012.04.084
(2012)
Synthesis, SAR study, and biological evaluation of a series of piperazine ureas as fatty acid amide hydrolase (FAAH) inhibitors

Doi:10.1016/j.bmc.2012.11.006
(2013)
Enzymes in Organic Synthesis: Remarkable Influence of a ? System on the Enantioselectivity in PPL Catalysed Monohydrolysis of 2-Substituted 1,3-Diacetoxypropanes.

Doi:10.1016/S0957-4166(00)82383-6
(1990)

Article Doi