Strict Reagent Control in the Asymmetric Allylboration of N-TIPS-α-Amino Aldehydes with the B-Allyl-10-TMS-9-borabicyclo[3.3.2]decanes

Autor:	Buddy Soto-Cairoli, John A. Soderquist
Rok vydání:	2008
Předmět:	Stereochemistry Chemistry Reagent Organic Chemistry Alpha (ethology) Organic chemistry Physical and Theoretical Chemistry Biochemistry
Zdroj:	Organic Letters. 11:401-404
ISSN:	1523-7052 1523-7060
DOI:	10.1021/ol802685e
Popis:	The allylboration of enantiomerically pure N-triisopropylsilyl-alpha-amino aldehydes (2) with B-allyl-10-trimethylsilyl-9-borabicyclo[3.3.2]decanes (1) proceeds cleanly at -78 degrees C, exhibiting essentially complete reagent control. After an oxidative workup, an HOAc-mediated N--O TIPS rearrangement facilitates the clean formation of stable O-TIPS protected beta-amino alcohol derivatives 3 which are isolated in 60-83% yields inor = 96% de and99% ee. For the leucinal series (R = i-Bu), an efficient entry to either statine (8aSS) or epi-statine (8aRS) is reported illustrating the versatility of this potent 1/2 combination.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::237a370d09b818866a4e70314098ab59 https://doi.org/10.1021/ol802685e Zobrazit plný text záznamu