Harmony of CdI2 with CuBr for the one-pot synthesis of optically active α-allenols

Organic & Biomolecular Chemistry
Jiasheng ZhangShengming Ma

Abstract

A highly efficient one-pot synthesis of chiral α-allenols from propargylic alcohols, aldehydes and pyrrolidine induced by CuBr and (R,Ra)-N-PINAP or (R,Sa)-N-PINAP and CdI2 has been developed. Both the yields and enantioselectivities of the allenols of this one-pot procedure are practical. Comparison with ZnI2 control experiments revealed that CdI2 can convert propargylic amine to allene in the presence of CuBr efficiently.

References

Mar 3, 2004·Angewandte Chemie·Anja Hoffmann-Röder, Norbert Krause
Jul 14, 2005·Chemical Reviews·Shengming Ma
Mar 11, 2006·The Journal of Organic Chemistry·Uli KazmaierManuela Klein
Jan 10, 2008·Organic Letters·Vanessa Kar-Yan LoChi-Ming Che
Oct 17, 2008·Accounts of Chemical Research·Malte BrasholzReinhold Zimmer
Jan 7, 2009·The Journal of Organic Chemistry·Jinqiang Kuang, Shengming Ma
Jul 17, 2009·Accounts of Chemical Research·Shengming Ma
Jan 28, 2010·Journal of the American Chemical Society·Jinqiang Kuang, Shengming Ma
Apr 27, 2010·Chemistry : a European Journal·Benito AlcaideTeresa Martínez del Campo
Jan 6, 2011·Chemistry : a European Journal·Fernando López, José Luis Mascareñas
Mar 12, 2011·Chemical Reviews·Corinne AubertAntoine Simonneau
Mar 17, 2011·Chemical Communications : Chem Comm·Shichao Yu, Shengming Ma
Sep 11, 2012·Angewandte Chemie·Baoqiang Wan, Shengming Ma
Nov 13, 2012·Chemistry : a European Journal·Juntao YeShengming Ma
Feb 21, 2013·Nature Chemistry·Takuya HashimotoKeiji Maruoka
Mar 16, 2013·Journal of the American Chemical Society·Ian T CrouchDoug E Frantz
Apr 24, 2013·Organic Letters·Ruizhi LüShengming Ma
Jul 23, 2013·Journal of the American Chemical Society·Yuli WangShengming Ma
Sep 18, 2013·Nature Communications·Xinjun TangShengming Ma
Jan 17, 2014·Accounts of Chemical Research·Benito Alcaide, Pedro Almendros
Feb 12, 2014·Chemical Society Reviews·S KitagakiC Mukai

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Citations

Jul 13, 2017·The Journal of Organic Chemistry·Maren Schaarschmidt, Klaus T Wanner
Jul 13, 2016·Chemistry : a European Journal·Xiaojun Huang, Alejandro Bugarin
Apr 4, 2019·The Journal of Organic Chemistry·Balaji V Rokade, Patrick J Guiry
Apr 16, 2019·Accounts of Chemical Research·Xin Huang, Shengming Ma
May 27, 2020·The Journal of Organic Chemistry·Runmin ZhaoYufen Zhao
Sep 23, 2021·ACS Omega·Leandros P ZorbaGeorgios C Vougioukalakis

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