(R)-2,3-Cyclohexylideneglyceraldehyde: a novel template for simple entry into both cis- and trans-2,5-disubstituted tetrahydrofurans
- 作者：Angshuman Chattopadhyay ; Prasad Vichare ; Bhaskar Dhotare
- 关键词：(R)-2 ; 3-Cyclohexylideneglyceraldehyde ; Sharpless asymmetric dihydroxylation ; Absolute stereoselectivity ; 2 ; 5-Disubstituted tetrahydrofurans ; Substrate controlled addition ; Stereodiversity
- 刊名：Tetrahedron Letters
- 出版年：2007
- 期刊代码：109_00404039
- 类别：ch
- 出版时间：16 April 2007
- 卷：48
- 期：16
- 页码：2871-2873
- 文件大小：120 K
摘要
Sharpless asymmetric dihydroxylation at the terminal olefin of benzoates 3a and 3b, using both AD-mix α and AD-mix β afforded only one diastereomer of diols 5a and 5b, respectively. Diols 5a and 5b were easily transformed into cis- and trans-2,5-disubstituted tetrahydrofurans 7 and 14, respectively, which were subsequently converted into known compounds 12 and 19.