Facile conversion of chromane-6-triflate to chromane-6-alanines under palladium conditions

TETRAHEDRON LETTERS

卷:54

Article

Miller, Daniel K.¹ 

[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

关键词: Palladium-catalyzed coupling;    Boronation;    Stannylation;    Aryl triflate;    Suzuki coupling;   

DOI  :  10.1016/j.tetlet.2012.11.115

来源: Elsevier

【 摘 要 】

Conversion of chromane-6-triflate 5 to chromane-6-dehydroalanine 9 or 10 via its Bpin-derivative 6 followed by Suzuki coupling with protected dehydroalanine bromides 7 or 8 were reported (86%). Alternatively, a palladium-catalyzed stannation of 5 with Bu6Sn2 afforded the tributyltin derivative 11, and iodination (12) followed by coupling with 13 gave chromane-6-alanine 15 (75%). Either approach constitutes a conversion from chromane-6-triflate to the corresponding protected chromane-6-alanine or its dehydro analog. (C) 2012 Elsevier Ltd. All rights reserved.

【 授权许可】

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