TY - JOUR AU - Loiseleur, Olivier; Cassayre, Jérôme; Leca, Dominique; Gaggini, Francesca; Pieniazek, Susan N.; Luft, Jennifer A. R.; Houk, Kendall N. TI - Control of Hetero-Diels–Alder Stereoselectivity through Solvent Polarity and Brønsted or Lewis Acid Catalysis; Theory and Experiment SN - 0936-5214 SN - 1437-2096 PY - 2013 JO - Synlett JF - Synlett LA - EN VL - 24 IS - 18 SP - 2446 EP - 2450 ET - 2013/10/18 DA - 2013/10/25 KW - spiroquinazoline alkaloids KW - stereoselectivity KW - Lewis acid catalysis KW - hetero-Diels–Alder KW - natural products AB - The stereoselectivity of cycloadditions involving 3-methyleneoxindole and 2-azadienes can be controlled by solvent polarity and by Lewis or Brønsted acid catalysis. The improvements in selectivity are advantageous for the synthesis of spiroquinazoline alkaloids such as alantrypinone and lapatin B. PB - © Georg Thieme Verlag DO - 10.1055/s-0033-1340046 UR - http://www.thieme-connect.de/products/ejournals/abstract/10.1055/s-0033-1340046 ER -