Dey Debanjana, Pathak Tanmaya
Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur 721302, India.
Molecules. 2016 May 26;21(6):690. doi: 10.3390/molecules21060690.
Enantiomerically pure 2-substituted-2,5-dihydro-3-(aryl) sulfonyl/sulfinyl furans have been prepared from the easily accessible carbohydrate derivatives. The orientation of the substituents attached at the C-2 position of furans is sufficient to control the diastereoselectivity of the addition of various nucleophiles to the vinyl sulfone/sulfoxide-modified tetrahydrofurans, irrespective of the size of the group. The orientation of the substituents at the C-2 center also suppresses the influence of sulfoxides on the diastereoselectivity of the addition of various nucleophiles. The strategy leads to the creation of appendage diversity, affording a plethora of enantiomerically pure trisubstituted furanics for the first time.
已从易于获得的碳水化合物衍生物制备了对映体纯的2-取代-2,5-二氢-3-(芳基)磺酰基/亚磺酰基呋喃。连接在呋喃C-2位的取代基的取向足以控制各种亲核试剂加成到乙烯基砜/亚砜修饰的四氢呋喃上的非对映选择性，而与基团大小无关。C-2中心处取代基的取向也抑制了亚砜对各种亲核试剂加成的非对映选择性的影响。该策略导致了附属物多样性的产生，首次提供了大量对映体纯的三取代呋喃类化合物。
