Synthesis of α‐Propargylglycinates Using the Borono‐Mannich Reaction with Pinacol Allenylboronate and Potassium Allenyltrifluoroborate. Issue 22 (14th July 2016)

• Record Type: Journal Article
• Authors: Chambers, Rachel K.; Chaipukdee, Nattapong; Thaima, Thanaphat; Kanokmedhakul, Kwanjai; Pyne, Stephen G.
• Is Part Of: European journal of organic chemistry. Issue 22(2016)
• Page Start: 3765
• Page End: 3772
• Publication Date: 2016-07-14
• Subjects: Synthetic methods -- Borono‐Mannich reaction -- Rerrangement -- Amino acids -- Alkynes; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201600436
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : The three component borono‐Mannich reactions of ethyl glyoxylate, primary or secondary amines and pinacol allenylboronate or potassium allenyltrifluoroborate are highly regioselective and give α‐propargylglycinates. The ( S )‐ N ‐ tert ‐butylsulfinyl imine of ethyl glyoxylate underwent an indium chloride catalyzed addition reaction with allenyl potassium trifluoroborate in a highly regioselective and diastereoselective manner to give ethyl ( S )‐α‐propargylglycinate after N ‐deprotection in 97 % ee . Abstract : A regioselective synthesis of α‐propargylglycinates using the borono‐Mannich reaction has been developed.