Tetrahedron

Stereoselective synthesis of spirocyclic oxindoles based on a one-pot Ullmann coupling/Claisen rearrangement and its application to the synthesis of a …

…, T Hirano, Y Okawa, A Nakazaki, S Kobayashi

Index: Miyamoto, Hiroshi; Hirano, Tomohiro; Okawa, Yoichiro; Nakazaki, Atsuo; Kobayashi, Susumu Tetrahedron, 2013 , vol. 69, # 45 p. 9481 - 9493

Full Text: HTML

Citation Number: 11

Abstract

Abstract An efficient and convenient approach to the synthesis of spirocyclic oxindoles from iodoindoles has been developed. The most striking feature of this approach is that the sequential intramolecular Ullmann coupling and Claisen rearrangement proceeds in a one- pot manner to afford 3-spiro-2-oxindoles in good yield with excellent diastereoselectivity. Application of this one-pot reaction to chiral non-racemic tertiary alcohol substrates ...

~88%

~87%

Efficient, one-pot transformation of indoles into functional...

[Lopez-Alvarado, Pilar; Steinhoff, Judith; Miranda, Sonia; Avendano, Carmen; Carlos Menendez Tetrahedron, 2009 , vol. 65, # 8 p. 1660 - 1672]

Organocatalyzed enantioselective fluorocyclizations

[Lozano, Oscar; Blessley, George; Martinez Del Campo, Teresa; Thompson, Amber L.; Giuffredi, Guy T.; Bettati, Michela; Walker, Matthew; Borman, Richard; Gouverneur, Veronique Angewandte Chemie - International Edition, 2011 , vol. 50, # 35 p. 8105 - 8109]

A versatile synthetic methodology for the synthesis of trypt...

[Garden, Simon J; Da Silva, Rosangela B; Pinto, Angelo C Tetrahedron, 2002 , vol. 58, # 42 p. 8399 - 8412]

Total synthesis of (±)-dragmacidin E

[Beck, Anthony L.; Mascal, Mark; Moody, Christopher J.; Coates, William J. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992 , # 7 p. 813 - 822]

A versatile synthetic methodology for the synthesis of trypt...

[Garden, Simon J; Da Silva, Rosangela B; Pinto, Angelo C Tetrahedron, 2002 , vol. 58, # 42 p. 8399 - 8412]