Enantioselective synthesis of (Z)-1,2-anti-2,5-anti-triol monosilyl ethers using a cross-metathesis allylboration sequence.
The enantioselective synthesis of (Z)-1,2-anti-2,5-anti-triol monosilyl ethers via a two-step sequence involving olefin cross-metathesis of β-alkoxyallylboronate 4 and subsequent allylboration of the derived bisboryl intermediate 6 provides triol monoethers 7 with good to excellent diastereoselectivity.
Winbush
SusAnn M
SM
Department of Chemistry, The Scripps Research Institute, Scripps Florida, Jupiter, Florida 33458, USA.
Roush
William R
WR
D001896:Boron Compounds / Q000737:chemistry*; D004987:Ethers / Q000138:chemical synthesis*; D015394:Molecular Structure; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
D001896:Boron Compounds; D004987:Ethers; D012821:Silanes
J Am Chem Soc. 2003 Dec 3;125(48):14901-4
14640667
Org Lett. 2008 Nov 6;10(21):4843-6
18837554
J Am Chem Soc. 2005 Dec 14;127(49):17160-1
16332044
J Am Chem Soc. 2002 Nov 20;124(46):13644-5
12431072
J Am Chem Soc. 2005 Jul 27;127(29):10406-11
16028954
Bioorg Med Chem. 1996 Aug;4(8):1271-9
8879548
Angew Chem Int Ed Engl. 2003 Apr 29;42(17):1900-23
12730969
Org Biomol Chem. 2010 Jan 21;8(2):398-406
20066276
Org Lett. 1999 Sep 23;1(6):953-6
10823227
Org Lett. 2005 Nov 24;7(24):5509-12
16288543
J Am Chem Soc. 2009 Nov 25;131(46):16905-18
19874023
J Am Chem Soc. 2009 Jan 28;131(3):1269-73
19117388
Org Lett. 2003 May 15;5(10):1697-700
12735755
J Am Chem Soc. 2004 Jun 23;126(24):7414-5
15198568
J Am Chem Soc. 2007 Mar 21;129(11):3070-1
17315879
Nat Protoc. 2007;2(10):2451-8
17947986
Chem Rev. 2003 Aug;103(8):2763-94
12914480
J Am Chem Soc. 2007 Jun 27;129(25):7961-8
17547403
J Am Chem Soc. 2009 Oct 14;131(40):14174-5
19775159
Org Lett. 2005 Mar 31;7(7):1411-4
15787519
J Org Chem. 2003 Jul 25;68(15):6031-4
12868943
Angew Chem Int Ed Engl. 2005 Jul 18;44(29):4490-527
16003791