Synthesis of homoallylic chiral tertiary alcohols via chelation-controlled diastereoselective nucleophilic addition on alpha-alkoxyketones: Application for the synthesis of the C-1-C-11 subunit of 8-epi-fostriecin

• Published in: Organic letters Vol. 5; no. 20; pp. 3755 - 3757
• Main Authors: Ramachandran, PV, Liu, HP, Reddy, MVR, Brown, HC
• Format: Journal Article
• Language: English
• Published: WASHINGTON Amer Chemical Soc 02.10.2003
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; REAGENTS; OLEFIN METATHESIS; ASYMMETRIC TOTAL-SYNTHESIS; PD 113,270; TUMOR AGENTS CI-920

Chiral beta-syn-alkoxyhomoallylic alcohols derived from alkoxyallylboration of aldehydes upon oxidation provided the corresponding chiral ketones. Chelation-controlled nucleophilic addition to these ketones occurred in a highly stereoselective manner to afford anti-homoallylic tertiary alcohols. Thi...