TY - JOUR AU - Hayashi, Yujiro; Toda, Shunsuke TI - Asymmetric Synthesis of Chiral 1,3-Dimethyl Units Through a Double Michael Reaction of Nitromethane and Crotonaldehyde Catalyzed by Diphenylprolinol Silyl Ether SN - 0936-5214 SN - 1437-2096 PY - 2019 JO - Synlett JF - Synlett LA - EN VL - 30 IS - 04 SP - 442 EP - 448 ET - 2019/01/16 DA - 2019/02/15 KW - organocatalyst KW - Michael reaction KW - asymmetric synthesis KW - diastereoselective reaction KW - diphenylprolinol silyl ether AB - An efficient synthetic route to install chiral 1,3-dimethyl units through a double Michael reaction of crotonaldehyde and nitromethane catalyzed by diphenylprolinol silyl ether is developed. Either 1,3-syn- or 1,3-anti-dimethyl units are obtained selectively depending on the enantiomer of the diphenylprolinol silyl ether catalyst used. The side chain of pneumocandin B0 is synthesized enantioselectively by using the present method as a key step. PB - Georg Thieme Verlag DO - 10.1055/s-0037-1611644 UR - http://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0037-1611644 ER -