Premium
Reversible P(III)/P(V) Redox: Catalytic Aza‐Wittig Reaction for the Synthesis of 4(3 H )‐Quinazolinones and the Natural Product Vasicinone
Author(s) -
Wang Long,
Wang Ying,
Chen Min,
Ding MingWu
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300950
Subject(s) - triphenylphosphine , wittig reaction , chemistry , phosphine , triphenylphosphine oxide , catalysis , phosphine oxide , medicinal chemistry , redox , natural product , combinatorial chemistry , organic chemistry
Abstract The catalytic aza‐Wittig reaction based on a phosphine/phosphine oxide catalytic cycle is reported. The by‐product triphenylphosphine oxide (Ph 3 PO) was reduced in situ to triphenylphosphine (Ph 3 P) with good chemselectivity so that the aza‐Wittig reaction can be accomplished by using merely a catalytic amount of triphenylphosphine. The reaction has been demonstrated in an efficient synthesis of 4(3 H )‐quinazolinones and the natural product ( S )‐vasicinone in high yields, by using a catalytic amount of triphenylphosphine (5%) and the tetramethyldisiloxane/titanium tetraisopropoxide [TMDS/Ti(O‐ i‐ Pr) 4 ] reductant system (81–95% yields and >99% ee ).