Efficient and selective synthesis of (S,R,R,S,R,S)-4,6,8,10,16,18-hexamethyl-docosane via Zr-catalyzed asymmetric carboalumination of alkenes (ZACA reaction).
(S,R,R,S,R,S)-4,6,8,10,16,18-Hexamethyldocosane (1) was synthesized in 11% yield in 11 steps in the longest linear sequence from > or =98% pure (S)-beta-citronellal and 6 additional steps for the preparation of 11 in 23% yield from propene. Five of the six asymmetric carbon centers were generated catalytically and stereoselectively by the ZACA reaction (5 times), one lipase-catalyzed acetylation, and two chromatographic operations.
Zhu
Gangguo
G
Herbert C. Brown Laboratories of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47907-2084, USA.
Liang
Bo
B
Negishi
Ei-ichi
E
D000473:Alkanes / Q000138:chemical synthesis* / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry*; D000535:Aluminum / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis
C519474:(S,R,R,S,R,S)-4,6,8,10,16,18- hexamethyldocosane; D000473:Alkanes; D000475:Alkenes; D002244:Carbon; D000535:Aluminum