American Chemical Society
ol5b02929_si_002.pdf (9 MB)

Catalytic Aldol–Cyclization Cascade of 3‑Isothiocyanato Oxindoles with α‑Ketophosphonates for the Enantioselective Synthesis of β‑Amino-α-hydroxyphosphonates

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journal contribution
posted on 2015-11-06, 00:00 authored by Satavisha Kayal, Santanu Mukherjee
A cascade aldol–cyclization reaction between 3-isothiocyanato oxindoles and α-ketophosphonates has been developed for the synthesis of β-amino-α-hydroxyphosphonate derivatives. Catalyzed by a quinine-based tertiary amino-thiourea derivative, this reaction delivers 2-thioxooxazolidinyl phosphonates based on a spirooxindole scaffold bearing two contiguous quaternary stereogenic centers in high yields with excellent diastereo- (up to >20:1 dr) and enantioselectivities (up to >99:1 er).