A facile and efficient one-pot synthesis of thiochromans from bis(2-formylphenyl) disulfide and alkenols via iodine-promoted generation and subsequent intramolecular cycloaddition of ortho-thiobenzoquinone methides

✍ Scribed by Takao Saito; Takahiro Horikoshi; Takashi Otani; Yosuke Matsuda; Takayuki Karakasa

• Book ID: 104254124
• Publisher: Elsevier Science
• Year: 2003
• Tongue: French
• Weight: 128 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(03)01510-7

✦ Synopsis

Stereoselective synthesis of tetrahydrofuro-and tetrahydropyrano[3,2-c]

benzothiopyrans was achieved by intramolecular [4+2]cycloaddition of o-thiobenzoquinone methides that were generated in situ from bis(2-formylphenyl) disulfide and alkenols in the presence of iodine under mild reaction conditions.