Jonathan Arkush became President of the Jewish Board of Deputies in 2015, which is the same year Jeremy Corbyn was elected leader of the Labour Party.
He has never previously directly accused the Labour leader of anti-Semitism but in an interview just before he steps down from his role on Friday, he said Mr Corbyn “has views which are anti-Semitic and he has problematic views”.
He added: “With the election of Jeremy Corbyn, it seemed people who had a habit of participating in anti-Semitic discourse thought some sort of space had opened up for them when they could say things that previously they knew they couldn’t.”
Mr Arkush was one of two Jewish leaders who met with Mr Corbyn to discuss the problem last month.
He spent two hours with the Labour leader along with President of the Jewish Leadership Council Jonathan Goldstein.
Mr Arkush said he confronted Mr Corbyn about his views and asked: “Why is there nothing good you can say about Israel? And he couldn’t answer.
“He was silent.”
The outgoing Jewish leader said it is time for Mr Corbyn to recognise “his real views about Israel”.
Speaking to the Telegraph, he added: “His associations are clear. He is a patron of Palestine Solidarity Campaign – if you look at its logo and language, it’s quite clear its world picture has no room for Israel.
“Delegitimising the state of Israel is anti-Semitic.
“He was a chairman of Stop the War, which is responsible for some of the worst anti-Israel discourse.
“He has never disavowed that sentiment. Is this double speak? What are we supposed to think?
“If he shares the prevalent discourse about Israel, then that view is unquestionably anti-Semitic.”
Mr Arkush said there is also anxiety among the Jewish community in the perceived growing rise in anti-Semitism which he thinks is the result of Mr Corbyn’s leadership.
He said it would also become worse if Mr Corbyn was elected Prime Minister unless he “took steps that were very clear that firmly, clearly and effectively addressed all forms of racism”.
Mr Corbyn is due to meet Jewish leaders in July but the Labour leader’s lack of action in stamping out anti-Semitism and kicking out members could derail the meeting.
He concluded: “We are not prepared to have meetings for the sake of meetings, which will confer some sort of spurious legitimacy on Labour’s attempts to deal with anti-Semitism.”
A spokesman for Mr Corbyn said: “These are unfounded and outrageous personal attacks without any evidence to support them.
“Jeremy has been absolutely clear that he is a militant opponent of anti-Semitism and is committed to driving it out of our movement.
“Our party has deep roots in the Jewish community and is campaigning to increase support and confidence in Labour among Jewish people in the UK.
“Jonathan Arkush’s attempt to conflate strong criticism of Israeli state policies with anti-Semitism is wrong and undermines the fight both against anti-Semitism and for justice for the Palestinians.
“It should be rejected outright.”