Catalytic asymmetric [4+2] cycloaddition of 1-((2-aryl)vinyl)naphthalen-2-ols with in situ generated ortho-quinone methides for the synthesis of polysubstituted chromanes. Issue 3 (11th December 2019)

• Record Type: Journal Article
• Authors: You, Yong; Li, Ting-Ting; Yuan, Shu-Pei; Xie, Ke-Xin; Wang, Zhen-Hua; Zhao, Jian-Qiang; Zhou, Ming-Qiang; Yuan, Wei-Cheng
• Is Part Of: Chemical communications. Volume 56:Issue 3(2020)
• Page Start: 439
• Page End: 442
• Publication Date: 2019-12-11
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c9cc08316b
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : An asymmetric [4+2] cycloaddition of 1-((2-aryl)vinyl)naphthalen-2-ols with in situ generated ortho -quinone methides enables the highly enantioselective synthesis of polysubstituted chromanes. Abstract : An efficient asymmetric [4+2] cycloaddition of 1-((2-aryl)vinyl)naphthalen-2-ols and in situ generated ortho -quinone methides with chiral phosphoric acid as the catalyst was developed. This reaction enables the highly enantioselective synthesis of chiral polysubstituted chromanes bearing multiple contiguous stereogenic centers in excellent yields and stereoselectivities (up to 99% yield, >95 : 5 dr and >99% ee).